[ CAS No. 88611-67-0 ] {[proInfo.proName]}

Name: 88611-67-0|N-(5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide|96%
Brand: Ambeed
SKU: A138937
Rating: 97 (35 reviews)

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Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 88611-67-0 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 88611-67-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 88611-67-0 ]

SDS Specification

Alternatived Products of [ 88611-67-0 ]

Product Details of [ 88611-67-0 ]

CAS No. :	88611-67-0	MDL No. :	MFCD00099461
Formula :	C₁₂H₁₃NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WEBCZGJWXXPNHB-UHFFFAOYSA-N
M.W :	203.24	Pubchem ID :	2780190
Synonyms :

Calculated chemistry of [ 88611-67-0 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	58.61
TPSA :	46.17 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.69 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.79
Log Po/w (XLOGP3) :	1.2
Log Po/w (WLOGP) :	1.97
Log Po/w (MLOGP) :	1.36
Log Po/w (SILICOS-IT) :	2.54
Consensus Log Po/w :	1.77

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.02
Solubility :	1.94 mg/ml ; 0.00955 mol/l
Class :	Soluble
Log S (Ali) :	-1.77
Solubility :	3.48 mg/ml ; 0.0171 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.79
Solubility :	0.0331 mg/ml ; 0.000163 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.76

Safety of [ 88611-67-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 88611-67-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 88611-67-0 ]
Downstream synthetic route of [ 88611-67-0 ]

[ 88611-67-0 ] Synthesis Path-Upstream 1~8

1
[ 3470-53-9 ]
[ 108-24-7 ]
[ 88611-67-0 ]

Reference： [1] Patent: WO2008/76336, 2008, A2, . Location in patent: Page/Page column 78
[2] Patent: WO2010/78427, 2010, A1, . Location in patent: Page/Page column 221

2
[ 50878-03-0 ]
[ 88611-67-0 ]

Reference： [1] Journal of Medicinal Chemistry, 1976, vol. 19, # 4, p. 472 - 475
[2] Journal of Organic Chemistry, 1962, vol. 27, p. 70 - 76

3
[ 14714-31-9 ]
[ 88611-67-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 18, p. 5539 - 5552

4
[ 2051-95-8 ]
[ 88611-67-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 18, p. 5539 - 5552

5
[ 6328-00-3 ]
[ 88611-67-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 18, p. 5539 - 5552

6
[ 88611-67-0 ]
[ 3470-53-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 11, p. 3436 - 3440
[2] Journal of Medicinal Chemistry, 1976, vol. 19, # 4, p. 472 - 475
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 21, p. 3482 - 3491
[4] Patent: EP1650202, 2006, A1, . Location in patent: Page/Page column 18

7
[ 88611-67-0 ]
[ 66361-67-9 ]

Reference： [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 21, p. 3482 - 3491

8
[ 88611-67-0 ]
[ 340825-13-0 ]

Reference： [1] Patent: WO2007/147762, 2007, A1,
[2] Patent: WO2007/147771, 2007, A2,

[ 88611-67-0 ] Synthesis Path-Downstream 1~88

1
[ 50878-03-0 ]
[ 88611-67-0 ]

Reference： [1]Journal of Medicinal Chemistry,1976,vol. 19,p. 472 - 475
[2]Journal of Organic Chemistry,1962,vol. 27,p. 70 - 76

2
[ 88611-67-0 ]
[ 3470-53-9 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; potassium hydroxide; water; for 9.0h;Heating / reflux;	Reference Example 6; 12.4 g of potassium hydroxide was added to a mixed solution of 9.0 g of 6-acetamidetetralone in 80 mL of methanol and 20 mL of water, and the system was refluxed under heating for 9 hours. After the reaction, reduced-pressure solvent distillation was performed, water was added, and extraction was performed with ethyl acetate. The extracted organic layer was washed with saturated brine and dried with magnesium sulfate, then subjected to reduced-pressure solvent distillation to obtain 6.5 g of 6-aminotetralone in the form of a dark brown solid. 6.8 mL of trifluoroacetic anhydride and 8.4 mL of triethylamine were added under ice cooling to 6.5 g of the compound obtained above in a 70 mL tetrahydrofuran solution, and the system was stirred for 4 hours under ice cooling. After the reaction, water was added under ice cooling, and extraction was performed with ethyl acetate. The extracted organic layer was washed with saturated brine and dried with magnesium sulfate, then subjected to reduced-pressure solvent distillation to obtain 10 g of 6-trifluoroacetamidetetralone (compound 2-29) in the form of a dark brown solid. [Show Image] MS m/z : 256 (M-H)- 1H NMR (200 MHz, CDCl3) delta (ppm):2.06-2.12 (m, 2H), 2.67 (t, J=6.2Hz, 2H), 2.99 (t, J=6.2Hz, 2H) 7.37 (dd, J=8.4, 2.0Hz, 1H), 7.70 (d, J=2.0Hz,1H), 8.07 (d, J=8.4Hz, 1H)

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3436 - 3440
[2]Journal of Medicinal Chemistry,1976,vol. 19,p. 472 - 475
[3]Journal of Medicinal Chemistry,1994,vol. 37,p. 3482 - 3491
[4]Patent: EP1650202,2006,A1 .Location in patent: Page/Page column 18

3
[ 298-12-4 ]
[ 88611-67-0 ]
[ 103602-85-3 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2277 - 2282

4
[ 298-12-4 ]
[ 88611-67-0 ]
[ 103602-85-3 ]

Reference： [1]Il Farmaco,1989,vol. 44,p. 967 - 974

5
[ 50-00-0 ]
[ 506-59-2 ]
[ 88611-67-0 ]
[ 103422-63-5 ]

Reference： [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 765 - 774

6
[ 50-00-0 ]
[ 506-59-2 ]
[ 88611-67-0 ]
[ 103422-63-5 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 2142 - 2148

7
[ 50-00-0 ]
[ 56609-03-1 ]
[ 88611-67-0 ]
N-[6-(4-Benzhydryl-piperazin-1-ylmethyl)-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl]-acetamide [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 2006 - 2015

8
[ 88611-67-0 ]
[ 74-88-4 ]
[ 149456-01-9 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 2121 - 2133

9
[ 88611-67-0 ]
[ 117013-78-2 ]
[ 107756-71-8 ]

Reference： [1]European Journal of Medicinal Chemistry,1987,vol. 22,p. 527 - 537
[2]Journal of Medicinal Chemistry,1992,vol. 35,p. 847 - 858

10
[ 88611-67-0 ]
[ 117013-79-3 ]
[ 107756-72-9 ]

Reference： [1]European Journal of Medicinal Chemistry,1987,vol. 22,p. 527 - 537

11
[ 88611-67-0 ]
[ 98709-76-3 ]

Reference： [1]Synthesis,2006,p. 133 - 145

12
[ 88611-67-0 ]
N-(2,2-dibromo-1,2,3,4-tetrahydro-1-oxonaphthalen-6-yl)acetamide [ No CAS ]

Reference： [1]Synthesis,2006,p. 133 - 145

13
[ 88611-67-0 ]
[ 1213300-87-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sulfuric acid; In water; at 90℃; for 0.75h;	Example 1N-(5-Aminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide The synthetic procedure described in this Example was carried out according to the process shown in Scheme C.SCHEME C Step 1 6-amino-3,4-dihydro-2H-naphthalen-l-oneA mixture of 2.5 grams (12.3 mmole) N-(5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)- acetamide in 20 mL 20% sulfuric acid was heated at 90 for 45 minutes. The solution was allowed to cool to room temperature, whereupon 6-amino-3,4-dihydro-2H-naphthalen-l- one sulfate precipitated as a solid mass. The solids were collected by filtration, washed with cold water and dried to give 1.92 g (97%) of 6-amino-3,4-dihydro-2H-naphthalen-l- one sulfate.
	With sulfuric acid; In water; at 90℃; for 0.75h;	Example 15 i^-[6-(3-Methoxy-benzenesulfonyl)-l,2,3lambda4-tetrahvdro-naphthalen-lylmethyll-methyl- amineThe synthetic procedure described in this Example was carried out according to the process shown in Scheme T.SCHEME TStep 1 6-Iodo-3,4-dihvdro-2ff-naphthalen- 1 -one <n="67"/>A mixture of N-(5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)-acetamide 2.5 grams (12.3 mmole) in 20 mL 20% sulfuric acid was heated at 90 for 45 minutes. The solution was allowed to cool to room temperature whereupon 6-amino-3,4-dihydro-2i-naphthalen- 1-one sulfate (not shown) precipitated as a solid mass. To this solid was added 20 mL water and 20 mL glacial acetic acid. The resulting solution was stirred in an ice bath and a solution of 1.72 grams (25 mmoles) sodium nitrite in 15 mL water was added dropwise over 0.5 hour. The reaction mixture was slowly poured into a well stirred solution of 8 grams (48 mmoles) potassium iodide in 80 mL water. The mixture was extracted with 200 mL ethyl ether, and the organic phase was washed with water, then saturated sodium hydrogen sulfite, then with saturated sodium chloride. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. The residue was subjected to low pressure column chromatography over silica gel 230-400 mesh eluting with 5% ethyl acetate in hexane. 6-Iodo-3,4-dihydro-2i-naphthalen-l-one was obtained as a white solid, 3.12 grams (94%), m.p. 77-78

Reference： [1]Patent: WO2007/147762,2007,A1 .Location in patent: Page/Page column 53
[2]Patent: WO2007/147771,2007,A2 .Location in patent: Page/Page column 65-66

14
[ 88611-67-0 ]
N-(2-chloro-1,2,3,4-tetrahydro-1-oxonaphthalen-6-yl)acetamide [ No CAS ]

Reference： [1]Synthesis,2006,p. 133 - 145

15
[ 88611-67-0 ]
N-(5,6-dihydronaphth[1',2':4,5]imidazo[1,2-a]pyridin-3-yl)acetamide [ No CAS ]

Reference： [1]Synthesis,2006,p. 133 - 145

16
[ 88611-67-0 ]
N-(5,6-dihydro-9-iodonaphth[1',2':4,5]imidazo[1,2-a]pyridin-3-yl)acetamide [ No CAS ]

Reference： [1]Synthesis,2006,p. 133 - 145

17
[ 88611-67-0 ]
N-(5,6-dihydro-9-bromonaphth[1',2':4,5]imidazo[1,2-a]pyridin-3-yl)acetamide [ No CAS ]

Reference： [1]Synthesis,2006,p. 133 - 145

18
[ 88611-67-0 ]
N-(5,6-dihydro-10-ethoxynaphth[1',2':4,5]imidazo[1,2-a]pyridin-3-yl)acetamide [ No CAS ]

Reference： [1]Synthesis,2006,p. 133 - 145

19
[ 88611-67-0 ]
[ 287719-93-1 ]

Reference： [1]Chemical Communications,2000,p. 763 - 764

20
[ 88611-67-0 ]
[ 287719-90-8 ]

Reference： [1]Chemical Communications,2000,p. 763 - 764

21
[ 88611-67-0 ]
N⁶-(3-dimethylamino-propyl)-13H-5,13-diaza-dibenzo[a,i]fluorene-6,10-diamine [ No CAS ]

Reference： [1]Chemical Communications,2000,p. 763 - 764

22
[ 88611-67-0 ]
[ 104120-90-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1999,vol. 36,p. 485 - 492
[2]Journal of Medicinal Chemistry,1989,vol. 32,p. 2277 - 2282

23
[ 88611-67-0 ]
8-aminobenzo<h>cinnolin-3(2H)-one [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1999,vol. 36,p. 485 - 492

24
[ 88611-67-0 ]
4-hydroxy-8-acetylamino-4,4a,5,6-tetrahydrobenzo<h>cinnolin-3(2H)-one [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1999,vol. 36,p. 485 - 492

25
[ 88611-67-0 ]
[ 66361-67-9 ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 3482 - 3491

26
[ 88611-67-0 ]
[ 125564-40-1 ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 3482 - 3491

27
[ 88611-67-0 ]
[ 158094-30-5 ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 3482 - 3491

28
[ 88611-67-0 ]
[ 103602-78-4 ]

Reference： [1]Il Farmaco,1989,vol. 44,p. 967 - 974
[2]Journal of Medicinal Chemistry,1989,vol. 32,p. 2277 - 2282

29
[ 88611-67-0 ]
[ 126681-69-4 ]

Reference： [1]Il Farmaco,1989,vol. 44,p. 967 - 974

30
[ 88611-67-0 ]
[ 103422-66-8 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2277 - 2282
[2]European Journal of Medicinal Chemistry,1990,vol. 25,p. 765 - 774

31
[ 88611-67-0 ]
[ 104107-08-6 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2277 - 2282
[2]European Journal of Medicinal Chemistry,1990,vol. 25,p. 765 - 774

32
[ 88611-67-0 ]
[ 103602-95-5 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2277 - 2282
[2]European Journal of Medicinal Chemistry,1990,vol. 25,p. 765 - 774

33
[ 88611-67-0 ]
[ 121866-04-4 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2277 - 2282

34
[ 88611-67-0 ]
[ 103602-97-7 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2277 - 2282

35
[ 88611-67-0 ]
[ 103602-95-5 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2277 - 2282

36
[ 88611-67-0 ]
[ 103602-89-7 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2277 - 2282

37
[ 88611-67-0 ]
[ 103602-91-1 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2277 - 2282

38
[ 88611-67-0 ]
[ 117013-80-6 ]

Reference： [1]European Journal of Medicinal Chemistry,1987,vol. 22,p. 527 - 537

39
[ 88611-67-0 ]
[ 117013-81-7 ]

Reference： [1]European Journal of Medicinal Chemistry,1987,vol. 22,p. 527 - 537

40
[ 88611-67-0 ]
[ 117013-70-4 ]

Reference： [1]European Journal of Medicinal Chemistry,1987,vol. 22,p. 527 - 537

41
[ 88611-67-0 ]
[ 117013-71-5 ]

Reference： [1]European Journal of Medicinal Chemistry,1987,vol. 22,p. 527 - 537

42
[ 88611-67-0 ]
[ 117013-95-3 ]

Reference： [1]European Journal of Medicinal Chemistry,1987,vol. 22,p. 527 - 537

43
[ 88611-67-0 ]
[ 117013-96-4 ]

Reference： [1]European Journal of Medicinal Chemistry,1987,vol. 22,p. 527 - 537

44
[ 88611-67-0 ]
[ 117014-08-1 ]

Reference： [1]European Journal of Medicinal Chemistry,1987,vol. 22,p. 527 - 537

45
[ 88611-67-0 ]
[ 117014-09-2 ]

Reference： [1]European Journal of Medicinal Chemistry,1987,vol. 22,p. 527 - 537

46
[ 88611-67-0 ]
N-[6-(4-Benzhydryl-piperazin-1-ylmethyl)-5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl]-acetamide [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 2006 - 2015

47
[ 88611-67-0 ]
[ 88411-91-0 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 2006 - 2015

48
[ 88611-67-0 ]
[ 88285-34-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 2006 - 2015

49
[ 88611-67-0 ]
[ 88285-35-2 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 2006 - 2015

50
[ 88611-67-0 ]
[ 88285-37-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 2006 - 2015

51
[ 88611-67-0 ]
[ 88285-39-6 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 2006 - 2015

52
[ 88611-67-0 ]
[ 88285-33-0 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 2006 - 2015

53
[ 88611-67-0 ]
N-[6-(4-Benzhydryl-piperazin-1-ylmethyl)-7,8-dihydro-naphthalen-2-yl]-propionamide [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 2006 - 2015

54
[ 88611-67-0 ]
[ 88285-36-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 2006 - 2015

55
[ 88611-67-0 ]
[ 138814-32-1 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 847 - 858

56
[ 88611-67-0 ]
[ 138814-33-2 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 847 - 858

57
[ 88611-67-0 ]
[ 138814-36-5 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 847 - 858

58
[ 88611-67-0 ]
[ 138834-44-3 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 847 - 858

59
[ 88611-67-0 ]
[ 138814-35-4 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 847 - 858

60
[ 88611-67-0 ]
[ 138814-34-3 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 847 - 858

61
[ 88611-67-0 ]
[ 104107-33-7 ]

Reference： [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 765 - 774

62
[ 88611-67-0 ]
[ 104107-34-8 ]

Reference： [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 765 - 774

63
[ 88611-67-0 ]
[ 103422-64-6 ]

Reference： [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 765 - 774

64
[ 88611-67-0 ]
[ 104107-09-7 ]

Reference： [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 765 - 774

65
[ 88611-67-0 ]
[ 104107-19-9 ]

Reference： [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 765 - 774

66
[ 88611-67-0 ]
[ 103422-89-5 ]

Reference： [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 765 - 774

67
paraformaldehyde [ No CAS ]
4-benzylpiperidin-4-ol hydrochloride [ No CAS ]
[ 88611-67-0 ]
(RS)-N-[6-(4-benzyl-4-hydroxy-piperidin-1-ylmethyl)-5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl]-acetamide hydrochloride [ No CAS ]

Reference： [1]Patent: US6359138,2002,B1 .Location in patent: Page column 23

68
[ 50-00-0 ]
[ 10024-89-2 ]
[ 88611-67-0 ]
[ 617246-39-6 ]

Yield	Reaction Conditions	Operation in experiment
50%	With acetic anhydride; In water; for 3.0h;Heating / reflux;	To morpholine hydrochloride (1.7g, 19.6 mmol) was added formaldehyde (1.6 mL, 37% w/v, 19.6 mmol) and the solution was allowed to stand for 1 h before slow addition to acetic anhydride (9.5 mL) Rapid addition leads to excessive exotherm. The mixture was then heated gently until complete solution was formed before the addition of N- (5-oxo- 5,6, 7, 8-tetrahydro-naphthalen-2-yl)-acetamide (2g, 9.8 mmol) and the solution was refluxed for 2h. After cooling, the volatiles were removed in vacuo. The oily residue was triturated with acetone leading to the precipitation of the title compound Ex 18 as its hydrochloride salt (1.46 g, 50%).'H NMR (CDCI3) s : 7.98 (1H, d, J8. 5), 7.75-7. 69 (2H, m), 7.24 (1 H, dd, J 8.5, 2.2), 3.68-3. 64 (4H, m), 2.85-1. 74 (11 H, m).

Reference： [1]Patent: WO2003/87046,2003,A1 .Location in patent: Page/Page column 48

69
[ 30354-18-8 ]
[ 88611-67-0 ]
[ 103422-63-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	In acetonitrile; at 85℃; for 4.0h;	To a solution of 6-acetamidotetralone (3.9 g, 19.2 mmol) in dry acetonitrile (80 ml) was quickly added, under an argon atmosphere, N-N-dimethylmethyleneiminium chloride (2.15 g, 23 mmol). The reaction mixture was stirred at 85C for 4 hours. After cooling, the precipitate was filtered off, washed with dry acetonitrile and dried in vacuo to give the title compound Ex 1 as a pale-yellow powder (5.41 g, 18.2 mmol, 95%).'H NMR (300 MHz, D20) : 8 2.10 (s, 3H), 2.90 (s, 6H), 7.29 (d, 1H), 7.39 (s, 1H), 7.83 (d, 1H) ; Melting point: 141-143C (uncorrected).

Reference： [1]Patent: WO2003/87046,2003,A1 .Location in patent: Page/Page column 41

70
[ 88611-67-0 ]
6-amino-3,4-dihydro-2H-naphthalen-1-one sulfate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; water; at 90℃; for 0.75h;	A mixture of N-(5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)-acetamide 2.5 grams (12.3 mmole) in 20 mL 20% sulfuric acid was heated at 90 for 45 minutes. The solution was allowed to cool to room temperature whereupon 6-amino-3,4-dihydro-2H- naphthalen-1-one sulfate (not shown) precipitated as a solid mass. To this solid was added 20 mL water and 20 mL glacial acetic acid. The resulting solution was stirred in an ice bath and a solution of 1.72 grams (25 mmoles) sodium nitrite in 15 mL water was added dropwise over 0.5 hour. The reaction mixture was slowly poured into a well stirred solution of 8 grams (48 mmoles) potassium iodide in 80 mL water. The mixture was extracted with 200 mL ethyl ether, and the organic phase was washed with water, then saturated sodium hydrogen sulfite, then with saturated sodium chloride. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. The residue was subjected to low pressure column chromatography over silica gel 230-400 mesh eluting with 5% ethyl acetate in hexane. 6-Iodo-3,4-dihydro-2H-naphthalen-l-one was obtained as a white solid, 3.12 grams (94%), m.p. 77-78.

Reference： [1]Patent: WO2006/66790,2006,A1 .Location in patent: Page/Page column 100; 101

71
[ 30354-18-8 ]
[ 88611-67-0 ]
6-Acetylamino-2-(N,N-dimethylamino)methyltetralin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium borohydrid; potassium carbonate;palladium-carbon; In tetrahydrofuran; methanol; acetonitrile;	REFERENCE EXAMPLE 31 6-Acetylamino-2-(N,N-dimethylamino)methyltetralin A THF solution (40 ml) of 6-acetylamino-1-tetralone (1.692 g) was added to an acetonitrile solution (40 ml) of N,N-dimethylmethylene ammonium chloride (2.04 g), then stirred at room temperature for 24 hours, and concentrated. An aqueous solution of 10% potassium carbonate was added to the residue, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried, and concentrated. The residue was dissolved in methanol (50 ml), to which was added sodium borohydride (0.86 g). The reaction mixture was stirred at room temperature for 1 hour, and water was added thereto, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried, and concentrated. The residue was dissolved in methanol (50 ml), to which were added 10% palladium-carbon (0.4 g) and 1 N hydrochloric acid (20 ml). Then, this was catalytically reduced under a hydrogen pressure of 1 atmosphere, for 12 hours. The palladium-carbon was removed from the reaction mixture through filtration, the filtrate was concentrated, and an aqueous solution of 10% potassium carbonate was added thereto to form a free form compound. Then, this was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried, and concentrated. The resulting crude crystals were recrystallized from ethyl acetate-hexane to obtain the entitled compound (1.862 g). m.p.: 104-107 C.

Reference： [1]Patent: US6310107,2001,B1

72
[ 88611-67-0 ]
[ 21568-65-0 ]
[ 149456-01-9 ]

Yield	Reaction Conditions	Operation in experiment
77%		PREPARATION 29 2,2-dimethyl-6-N-methylacetamido-1,2,3,4-tetrahydronaphthalen-1-one Following the procedure described in preparation 4, but starting from <strong>[88611-67-0]6-acetamido-1,2,3,4-tetrahydronaphthalen-1-one</strong> (N. L. Allinger, E. S. Jones, J. Org. Chem., 1962, 27, 70), the title compound of this preparation was obtained as a white solid (yield: 77%). M.p.: 92.2-94.3 C.; IR (KBr) nu: 2959, 2915, 1670, 1649, 1593, 1377, 1300, 1215, 967 cm-1; 1 H NMR (80 MHz, CDCl3) delta (TMS): 8.09 (d, J=8 Hz, 1H, Ar), 7.16 (m, 2H, Ar), 3.28 (s, 3H, CH3 N), 3.00 (t, J=6.3 Hz, 2H, CH2 Art), 2.01 (t, J=6.3 Hz, 2H, CH2), 1.96 (s, 3H, CH3 CO), 1.24 (s, 6H, 2 CH3).

Reference： [1]Patent: US5208246,1993,A

73
[ 4637-24-5 ]
[ 88611-67-0 ]
[ 331760-33-9 ]

Yield	Reaction Conditions	Operation in experiment
	at 110℃; for 2.0h;	EXAMPLE 414'-Chloro-N-[6-[(N,N-dimethyl)methyl]-7,8-dihydro-2-naphthalenyl][1,1'-biphenyl]-4-carboxamide; 1) <strong>[88611-67-0]6-Acetamido-1-tetralon</strong>e (5.0 g, 0.0246 mol) synthesized according to a known method by documents (Journal of Organic Chemistry 27, 70 (1962)), was dissolved in 50 ml of DMF dimethylacetal, which was stirred at 110 C. for 2 hours. The precipitate was collected by filtration, and washed with ethyl acetate to give 6-acetamido-2-(N,N-dimethylaminomethylidene)-1-tetralone (4.98 g) as a yellow powder.1H-NMR (CDCl3) delta: 2.19 (3H, s), 2.79-2.83, (2H, m), 2.88-2.92 (2H, m), 3.11 (6H, s), 7.14-7.17 (1H, m7.68 (1H, s), 7.69 (1H, s), 7.95 (1H, d, J=8.1 Hz), 7.96 (1H, s).Melting point: 207-210 C. (crystallization solvent: ethyl acetate)2) The obtained 6-acetamido-2-(N,N-dimethylaminomethylidene)-1-tetralone (4.50 g, 0.0173 mol) was dissolved in methanol (50 ml), and sodium borohydride (6.56 g, 0.173 mol) was added to the solution under ice-cooling, which was stirred for 2 hours. The reaction mixture was concentrated. Ethyl acetate and sodium hydrogencarbonate solution were added to the residue, and extraction was conducted. The ethyl acetate layer was concentrated, and 30 ml of tetrahydrofuran and 30 ml of 2N hydrochloric acid were added to the residue, which was refluxed with heating for 16 hours. The reaction mixture was concentrated, and ethyl acetate and 2N sodium hydroxide solution were added, and extraction was conducted. The ethyl acetate layer was concentrated, and the residue was refined using alumina column chromatography (development solvent; ethyl acetate:n-hexane=30:70), to give 6-[(N,N-dimethylamino)methyl]-7,8-dihydro-2-naphthaleneamine (1.60 g) as a colorless oily substance.1H-NMR (CDCl3) delta: 2.23 (6H, s), 2.28 (2H, t, J=8.4 Hz), 2.74 (2H, t, J=8.4 Hz), 2.95 (2H, s), 3.57-3.72 (2H, m), 6.25 (1H, s), 6.46-6.48 (2H, m), 6.83 (1H, d, J=8.7 Hz).3) The titled compound (1.12 g) was obtained as a white powder by the same method as in Example 1, using the obtained 6-[(N,N-dimethylamino)methyl]-7,8-dihydro-2-naphthalenamine (1.00 g, 0.005 mol), and 4-chlorobiphenyl carboxylic acid (2.31 g, 0.01 mol).1H-NMR (CDCl3) delta: 2.25 (6H, s), 2.34 (2H, t, J=7.8 Hz), 2.86 (2H, t, J=7.8 Hz), 2.99 (2H, s), 6.34 (1H, s), 7.03 (1H, d, J=8.7 Hz), 7.39 (1H, d, J=8.1 Hz), 7.45 (2H, d, J=8.7), 7.48 (1H, s), 7.56 (2H, d, J=8.4 Hz), 7.67 (2H, d, J=8.4 Hz), 7.78 (1H, s), 7.94 (2H, d, J=8.4 Hz).Elemental analysis for C26H25ClN2O Calcd.: C, 74.90; H, 6.04; N. 6.72. Found: C, 74.64; H, 6.14; N, 6.56.Melting point: 204-207 C. (crystallization solvent: ethyl acetate-n-hexane)

Reference： [1]Patent: US7115750,2006,B1 .Location in patent: Page/Page column 134-135

74
[ 88611-67-0 ]
[ 1034921-27-1 ]

Yield	Reaction Conditions	Operation in experiment
		b) 3-(6-Acetylamino-1 ,2,3,4-tetrahydro-naphthalen-1 -yl)-3H-imidazole-4-carboxylic acid isopropyl ester; To a solution of lambda/-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide (1.00 g, 4.94 mmol) in methanol (20 mL) at 0 0C is added sodium borohydride (0.50 g, 7.41 mmol). The reaction is stirred for 1.5 hours, whereupon water is added and the volatiles are removed in vacuo. The mixture is extracted with dichloromethane and the organic phase is dried over sodium sulfate, filtered, and concentrated to give lambda/-(5-hydroxy-5,6,7,8-tetrahydro- naphthalen-2-yl)-acetamide, which is used in the next step without further purification.
		REFERENCE EXAMPLE 716-Acetamido-2-tetralone; 1) Sodium borohydride (931 mg, 24.6 mmol) was added to a methanol solution (60 ml) of <strong>[88611-67-0]6-acetamido-1-tetralone</strong> (5.00 g, 24.6 mmol) under ice-cooling, which was stirred at room temperature for 1 hour. Ethyl acetate was added to the reaction mixture, which was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then, the solvent was distilled out under reduced pressure. p-Toluenesulfonic acid (468 mg, 2.46 mmol) and toluene (120 ml) were added to the obtained alcohol form (5.05 g, 24.6 mmol), which was stirred at 100 C. for 1 hour. The solvent was distilled out under reduced pressure. Ethyl acetate was added to the residue, which was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The resulting oily substance was purified by silica gel column chromatography (development solvent; hexane:ethyl acetate=1:1), and powdered with hexane to give N-(7,8-dihydro-2-naphthalenyl)acetamide (3.17 g).1H NMR (CDCl3): 2.16 (3H, s), 2.29 (2H, m), 2.28 (2H, m), 5.97 (1H, m), 6.42 (2H, d, J=9.6 Hz), 6.97 (1H, d, J=8.1 Hz), 7.14 (1H, br), 7.20 (1H, m), 7.32 (1H, s).2) m-Chloroperbenzoic acid (5.13 g, 20.8 mmol) was added to a chloroform solution (80 ml) of N-(7,8-dihydro-2-naphthalenyl)acetamide (3.00 g, 16.0 mmol) obtained in 1) under ice-cooling, which was stirred at room temperature for 2 hours. Ethyl acetate was added to the reaction mixture, which was washed with saturated sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The resulting oily substance was purified by alumina B column chromatography (development solvent; hexane:ethyl acetate=1:1). 1N Sodium hydroxide solution (10.7 ml) was added to a methanol solution (100 ml) of the obtained oily substance (3.20 g, 8.89 mmol) under ice-cooling, which was stirred at room temperature for 30 minutes. The solvent was distilled out under reduced pressure. Ethyl acetate was added to the residue, which was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The resulting oily substance was purified by alumina B column chromatography (development solvent; ethyl acetate: methanol=10:1). p-Toluenesulfonic acid (50 mg, 0.262 mmol) and toluene (26 ml) were added to the obtained diol (596 mg, 2.62 mmol), which was stirred at 120 C. for 3 hours. The solvent was distilled out under reduced pressure. Ethyl acetate was added to the residue, which was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The resulting oily substance was purified by silica gel column chromatography (development solvent; hexane:ethyl acetate=1:3), and powdered with diisopropyl ether, to give the titled compound (231 mg).1H NMR (CDCl3) delta: 2.18 (3H, s), 2.54 (2H, m), 3.04 (2H, m), 3.76 (2H, s), 7.06 (1H, d, J=8.1 Hz), 7.21 (1H, dd, J=8.1, 2.0 Hz), 7.31 (1H, br), 7.61 (1H, d, J=2.0 Hz).

Reference： [1]Patent: WO2008/76336,2008,A2 .Location in patent: Page/Page column 78-79
[2]Patent: US7115750,2006,B1 .Location in patent: Page/Page column 91-92

75
[ 30354-18-8 ]
[ 88611-67-0 ]
[ 103422-63-5 ]

Yield	Reaction Conditions	Operation in experiment
		REFERENCE EXAMPLE 666-[(Dimethylamino)methyl]-5-methyl-7,8-dihydro-2-naphthalenamine; 1) 6-Acetylamino-1-tetralone (5.5 g, 0.027 mol) and dimethylmethylenammonium chloride (6.3 g, 0.068 mol) were dissolved in a mixed solution of acetonitrile (100 ml) and tetrahydrofuran (100 ml), which was stirred for 48 hours. The crystallized product was collected by filtration, washed with tetrahydrofuran, and dissolved in ethyl acetate. 0.5N Sodium hydroxide solution was added to the solution for liquid separation. The organic layer was concentrated, to give 6-acetylamino-2-[(dimethylamino)methyl]-1-tetralone (4.48 g) as a colorless oily substance.2) 6-Acetylamino-2-[(dimethylamino)methyl]-1-tetralone (260 mg, 1.00 mmol) obtained was dissolved in tetrahydrofuran (10 ml). 1M Methyl magnesium bromide tetrahydrofuran solution (3 ml) (3.00 mmol) was added to the solution under ice-cooling, which was stirred at room temperature for 16 hours. Aqueous ammonium chloride solution was added to the reaction mixture, and extraction was conducted using ethyl acetate. The organic layer was concentrated, and 5N hydrochloric acid and ethyl acetate were added to the residue for liquid separation. Concentrated hydrochloric acid was added to the water layer, which was refluxed for 4 hours. The reaction mixture was concentrated, and 1N sodium hydroxide solution and ethyl acetate were added to the residue and extraction was conducted. The organic layer was concentrated, and the residue was purified by alumina column chromatography (development solvent; ethyl acetate n-hexane=3:7), to give the titled compound (83 mg) as a colorless oily substance.1H-NMR (CDCl3) delta: 2.04 (3H, s), 2.24 (6H, s), 2.28 (2H, t, J=7.4 Hz), 2.66 (2H, t, J=7.4 Hz), 3.04 (2H, s), 3.62 (2H, s), 6.49 (1H, s), 6.51-6.55 (1H, m), 7.10 (1H, d, J=8.1 Hz).

Reference： [1]Patent: US7115750,2006,B1 .Location in patent: Page/Page column 88-89

76
CH₃ [ No CAS ]
[ 124-63-0 ]
[ 88611-67-0 ]
[ 66361-80-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In pyridine;	EXAMPLE 189 6-Methylsulfonamido-1-tetralone A mixture of <strong>[88611-67-0]6-acetamido-1-tetralone</strong> (50 g) and 6 N HCl (400 ml) was heated at reflux for 2 hours, cooled and extracted with Et2 O. The aqueous phase was basified with ammonium hydroxide upon which a precipitate formed. The solid was collected, dried under vacuum and chromatographed on silica gel (elution with CH2 Cl2 followed by 1% CH3 OH/CH2 Cl2) to provide 22.1 g of the amino derivative. To a solution of the above amino derivative (7.0 g) in pyridine (40 ml) at 0 C. was added dropwise methanesulfonyl chloride (3.7 ml) and the resulting mixture allowed to stir at 0 C. for 45 minutes. The reaction was then warmed to room temperature and allowed to stir for 30 minutes. The reaction was poured into ice/con. HCl, upon which a precipitate formed. The solid was collected to afford 9.11 g of the desired compound.

Reference： [1]Patent: US5086074,1992,A

77
[ 7677-24-9 ]
[ 88611-67-0 ]
[ 107756-66-1 ]

Yield	Reaction Conditions	Operation in experiment
	aluminium trichloride; toluene-4-sulfonic acid; In ethyl acetate; toluene; benzene;	EXAMPLE 72 6-Acetamido-1-cyano-(3,4-dihydronaphthalene) <strong>[88611-67-0]6-Acetamido-1-tetralon</strong>e (4 g) was suspended in benzene (20 ml) and trimethylsilyl cyanide (3.2 ml) added. A catalytic amount of aluminum chloride was added and the reaction heated at 80 C. under nitrogen for 3 hours, then additional trimethylsilyl cyanide (3.2 ml) was added and reaction heated to 110 for 1 hour. The volatiles were removed in vacuo and the residue purified on a short silica column to afford the trimethylsilyl cyanide adduct 4.75 g (79%) which was dissolved in toluene (150 ml). A catalytic amount of p-toluenesulfonic acid was added and the reaction mixture was refluxed for 1 hour, cooled, and the solvent evaporated. The residue was dissolved in ethyl acetate and washed successively with 5% NaHCO3, brine, dried and evaporated to yield 2.9 g of a brown oil.
	With zinc(II) iodide; In benzene;Reflux;	Step A: N- (5-cyano-7 ,8-dihydronaphthalen-2-yl)acetamide: N-(5-oxo-5,6,7 , 8-tetrahydronaphthalen-2-yl)acetamide (5.00 g, 24.6 mmol) was dissolved in benzene then zinc iodide (0.079 g, 0.246 mmol) and trimethylsilylcyanide (6.56 mL, 49.2 mmol) were added and the mixture was refluxed for 1 h. Next, the benzene was evaporated off and isopropanol -HC1 saturated solution (20 ml) was added to the residue and and the mixture was refluxed for 1 hr. The suspension was stuffed overnight. The reaction was poured into water and extracted withethyl acetate (2x). The organic layer was washed with iN NaOH (lx), iN HC1 (lx), brine (lx)then dried and evaporated to dryness. The residue was purified by chromatography through a330g ISCO Redi-Sep with 5%MeOH/DCM solvent system to yield N-(5-cyano-7, 8-dihydronaphthalen-2-yl) acetamide. LC-MS: M+1= 213.

Reference： [1]Patent: US4634705,1987,A
[2]Patent: WO2014/99633,2014,A2 .Location in patent: Page/Page column 92

78
[ 88611-67-0 ]
[ 107756-71-8 ]

Yield	Reaction Conditions	Operation in experiment
8.73 g (48%)	With nitric acid;	EXAMPLE 81 6-Acetamido-5-nitro-1-tetralone 6-Acetamido-tetralone (15 g) was added in small portions to a cold solution of nitric acid (46 ml) at -30 C. After the addition was complete (2-3 hours), the reaction mixture was stirred at the same temperature for 1 hour, warmed to 0 C. and stirred for 4 hours. The reaction was poured on ice, basified with aqueous sodium hydroxide and extracted with ethyl acetate several times. The organic layer was separated, dried and evaporated. The desired 5-nitro-isomer was separated using flash chromatography (ethyl acetate-methylene chloride) to afford 8.73 g (48%).

Reference： [1]Patent: US4634705,1987,A

79
[ 872-53-7 ]
[ 88611-67-0 ]
[ 1023650-21-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	With pyrrolidine; In methanol; at 20 - 55℃;	Preparation 36; N-(6-(cyclopentylmethylene)-5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide; A mixture of 6-acetamido-i-tetralone (Ryan Scientific) (200 mg, 0.98 mmol) and cyclopentanecarboxaldehyde (0.21 ml_, 1.9 mmol) in methanol (2 mL) was treated with pyrrolidine (0.25 mL, 2.9 mmol) at room temperature for 1 hour then heated at 55 0C overnight. The mixture was cooled to room temperature, treated with 1N hydrogen chloride (4 mL) was filtered thru a Chem Elute tube (CE101 1) eluting with 90% dichloromethane / 10% ethyl acetate and condensed filtrate to give (E)-N-(6-(cyclopentylmethylene)-5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide (200 mg, 0.71 mmol, 72%n yield) as a tan foam. 1H NMR (400 MHz, DMSOd6) delta ppm 1.25 - 1.44 (m, 2 H), 1.52 - 1.76 (m, 4 H), 1.77 - 1.90 (m, 2H), 2.08 (s, 3 H), 2.70 - 2.92 (m, 5 H), 6.63 (d, J=9.67 Hz, 1 H), 7.49 (dd, J=8.59, 2.15 Hz, 1 H), 7.59 - 7.66 (m, 1 H), 7.86 (d, J=8.59 Hz, 1 H), 10,23 (s, 1 H). ES-MS m/z 284 (M+H).

Reference： [1]Patent: WO2008/53300,2008,A1 .Location in patent: Page/Page column 70-71

80
[ 3470-53-9 ]
[ 108-24-7 ]
[ 88611-67-0 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; for 1.0h;	a) lambda/-(5-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide; To a solution of 6-amino-3,4-dihydro-2H-naphthalen-1-one (CASNo. 3470-53-9, 0.875 g, 5.44 mmol) in pyridine (5 ml_) is added acetic anhydride (0.83 g, 8.16 mmol). After 1 hour, the solution is diluted with dichloromethane and washed with water and 1M aqueous HCI. The organic phase is dried over sodium sulfate, filtered, and concentrated to give lambda/-(5-oxo- 5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide; 1H NMR (400 MHz, CDCI3) delta ppm 2.09 - 2.16 (m, 2 H), 2.22 (s, 3 H), 2.59 - 2.67 (m, 2 H), 2.95 (t, J=6.1 Hz, 2 H), 7.21 (dd, J=8.3, 2.1 Hz, 1 H), 7.42 (br. s., 1 H), 7.70 (br. s., 1 H), 8.00 (d, J=8.3 Hz, 1 H).
	With pyridine; at 20℃; for 3.0h;	Step 1 : Synthesis of N-(5-oxo-5,6, 7, 8-tetrahydronaphthalen-2-yl)acetamide. To a solution of 6-amino-3,4-dihydronaphthalen-l(2H)-one (0.5 g, 3.1 mmol) in pyridine (5mL) was added acetic anhydride (0.38 g,3.7 mmol). The solution was stirred at room temperature for 3 hours. The reaction was then diluted with dichloromethane (50 mL). The organic layer was separated, washed with 2M HCl (2 x 25 mL), brine (50 mL), dried using sodium sulfate and concentrated under reduced pressure. The crude was product was obtained as an off colored solid (0.5 g, 79%) and used in the next reaction without any further purification. 1H NMR (CDCl3, 400MHz): delta 8.94 (d, J= 8.0 Hz, IH), 7.72 (s, IH), 7.62 (s, IH), 7.20 (d, J= 8.0 Hz, IHO, 2.96 (t, J= 6.2 Hz, 2H), 2.62 (quintet, J= 6.0 Hz, 2H), 2.12 (s, 3H), 2.11 (t, J= 6.0 Hz, 2H); LCMS [M+H]: 204.

Reference： [1]Patent: WO2008/76336,2008,A2 .Location in patent: Page/Page column 78
[2]Patent: WO2010/78427,2010,A1 .Location in patent: Page/Page column 221

81
C₁₂H₁₂ClNO₃ [ No CAS ]
[ 88611-67-0 ]

Yield	Reaction Conditions	Operation in experiment
800 mg		To fuming nitric acid (1000 mL) was added portionwise 4-oxo-4-phenylbutanoic acid (200 g, 1.12 mol) at ice-bath cooling and the reaction mixture was stirred for 2 h. The solution was poured into ice. The resulting precipitates were collected and washed with water, ethanol and isopropyl ether. The solid was recrystallized from hot EtOAc to afford 4-(3-nitrophenyl)-4-oxobutanoic acid (157 g, 63%) as a white solid.CommentA mixture of 4-(3-nitrophenyl)-4-oxobutanoic acid (20.0 g, 87.3 mmol) and 10% Pd/C (4.0 g) in acetic acid (500 mL) was maintained under 0.4 Mpa of hydrogen for 3 h at room temperature. Concentrated HCl (9.0 mL) was added to the solution and the mixture was maintained under 0.4 Mpa of hydrogen for 4 h continuously. The catalyst was filtered off and the filtrate was concentrated in vacuo. The residue was washed with EtOAc to afford 4-(3-aminophenyl)butanoic acid hydrochloride (18.4 g, 98%) as a white solid.CommentAcetic anhydride (12.3 mL, 131 mmol) was added dropwise to a solution of 4-(3-aminophenyl)butanoic acid hydrochloride (23.5 g, 109 mmol) in pyridine (250 mL) and the reaction mixture was stirred for 1 h at room temperature. The solution was concentrated in vacuo and the residue was dissolved with EtOAc. The solution was washed with 4 M HCl and brine. The extracts were dried (Na2SO4) and the solvent was evaporated in vacuo. The residue was recrystallized from EtOAc and hexane to give 4-[3-(acetylamino)phenyl]butanoic acid (22.6 g, 94%) as a white solid.CommentTo a suspension of 4-[3-(acetylamino)phenyl]butanoic acid (1.00 g, 4.52 mmol) in nitromethane (20 mL) was added thionyl chloride (361 muL, 4.97 mmol) at ice-bath cooling and the reaction mixture was stirred for 1 h. Aluminum chloride (1.51 g, 11.3 mmol) was added portionwise to this solution at room temperature. The reaction mixture was stirred for 30 min, poured into ice, and extracted with EtOAc. The extracts were washed with brine, 4 M NaOH and brine again. The extracts were dried (Na2SO4) and the solvent was evaporated in vacuo. The residue was recrystallized from EtOAc and hexane to give 3 (800 mg, 87%) as a white solid. 1H NMR (CDCl3) delta: 2.07-2.16 (2H, m), 2.21 (3H, s), 2.62 (2H, t, J = 6.0 Hz), 2.94 (2H, t, J = 6.0 Hz), 7.19-7.22 (1H, m), 7.57 (1H, br s), 7.69 (1H, s), 7.97 (1H, d, J = 8.4 Hz).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 5539 - 5552

82
[ 14714-31-9 ]
[ 88611-67-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 5539 - 5552

83
4-(3-amino-phenyl)-4-oxo-butyric acid ; hydrochloride [ No CAS ]
[ 88611-67-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 5539 - 5552

84
[ 4637-24-5 ]
[ 88611-67-0 ]
6-amino-2-[(dimethylamino)methylidene]-3,4-dihydro-1(2H)-naphthalenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	at 100℃; for 18.0h;Inert atmosphere;	A mixture of dimethylformamide dimethylacetal (100 mL) and 3 (16.5 g, 81.3 mmol) was heated at 100 C for 18 h under N2. The mixture was cooled to room temperature and diluted with EtOAc. The resulting precipitates were collected and washed with EtOAc to afford 4a (17.9 g, 84%) as a yellow solid, mp 207-210 C (EtOAc). 1H NMR (CDCl3) delta: 2.19 (3H, s), 2.79-2.83 (2H, m), 2.88-2.92 (2H, m), 3.11 (6H, s), 7.14-7.17 (1H, m), 7.68 (1H, s), 7.69 (1H, s), 7.95 (1H, d, J = 8.1 Hz), 7.96 (1H, s).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 5539 - 5552

85
[ 2051-95-8 ]
[ 88611-67-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 5539 - 5552

86
[ 6328-00-3 ]
[ 88611-67-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 5539 - 5552

87
[ 88611-67-0 ]
[ 107756-67-2 ]

Reference： [1]Patent: WO2014/99633,2014,A2

88
[ 88611-67-0 ]
[ 340825-13-0 ]

Reference： [1]Patent: WO2007/147762,2007,A1

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 88611-67-0 ] {[proInfo.proName]}

Quality Control of [ 88611-67-0 ]

Related Doc. of [ 88611-67-0 ]

Product Details of [ 88611-67-0 ]

Calculated chemistry of [ 88611-67-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 88611-67-0 ]

Application In Synthesis of [ 88611-67-0 ]

[ 88611-67-0 ] Synthesis Path-Upstream 1~8

[ 88611-67-0 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 88611-67-0 ]

Aryls

Amides

Ketones

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 88611-67-0 ]