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Quality Control of 6-Amino-2-naphthoic acid Purity: 97% SDS Specification

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Product Details of 6-Amino-2-naphthoic acid

CAS No. :	116668-47-4
Formula :	C₁₁H₉NO₂
M.W :	187.19
SMILES Code :	O=C(O)C1=CC=C2C=C(N)C=CC2=C1
MDL No. :	MFCD01861831
InChI Key :	NZTPZUIIYNYZKT-UHFFFAOYSA-N
Pubchem ID :	2733954

Safety of 6-Amino-2-naphthoic acid

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of 6-Amino-2-naphthoic acid

* 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 [ 116668-47-4 ]
Downstream synthetic route of [ 116668-47-4 ]

[ 116668-47-4 ] Synthesis Path-Upstream 1~1

1
[ 116668-47-4 ]
[ 5042-97-7 ]

References: [1] Patent: WO2004/48314, 2004, A1, . Location in patent: Page 45-46.
[2] Patent: WO2006/85118, 2006, A2, . Location in patent: Page/Page column 29.

[ 116668-47-4 ] Synthesis Path-Downstream 1~35

1
[ 24424-99-5 ]
[ 116668-47-4 ]
[ 516465-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; NaOH; In water; tert-butyl alcohol;	Example 4.1Synthesis of 6-(tert-butoxycarbonylamino)-2-naphthoic acid (7)Boc2O (280 mg, 1.28 mmol) and NaOH (40 mg, 1.0 mmol) were added to a solution of <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> (200 mg, 1.07 mmol) in t-BuOH (6 mL) and H2O (6 mL).The reaction mixture was stirred at room temperature for 12 hours, after which it was diluted with water and washed with CH2Cl2.The aqueous layer was adjusted to a pH level of about 2 with 2N HCl and extracted with ethyl acetate.The organic layer was dried over Na2SO4, and the filtrate was concentrated and purified by silica column chromatography (ethyl acetate/hexane=1/1) (300 mg, 98percent).1H-NMR (CD3OD) 8.48 (s, 1H), 8.05 (s, 1H), 7.95 (d, J=8.4, 1H), 7.86 (d, J=8.7, 1H), 7.75 (d, J=8.7, 1H), 7.51 (d, J=8.8, 1H) 1.53 (s, 9H) ppm; ESI-MS m/z calcd for C16H17N2O: 287.3105. found 288.8273 [M+1].

References: [1]Chemical Communications,2010,vol. 46,p. 722 - 724.
[2]Journal of Medicinal Chemistry,2005,vol. 48,p. 7024 - 7039.
[3]Patent: US2012/128592,2012,A1 .

2
[ 95-24-9 ]
[ 116668-47-4 ]
[ 530-62-1 ]
6-[3-(6-chloro-benzothiazol-2-yl)-ureido]-naphthalene-2-carboxylic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4657 - 4660.

3
[ 116668-47-4 ]
[ 530-62-1 ]
[ 1744-22-5 ]
6-[3-(6-trifluoromethoxy-benzothiazol-2-yl)-ureido]-naphthalene-2-carboxylic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4657 - 4660.

4
[ 67-56-1 ]
[ 116668-47-4 ]
[ 5159-59-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5033 - 5036.
[2]Journal of Medicinal Chemistry,2006,vol. 49,p. 7108 - 7118.
[3]Journal of the American Chemical Society,2008,vol. 130,p. 16836 - 16837.
[4]Journal of Molecular Structure,2008,vol. 891,p. 346 - 350.
[5]Journal of Polymer Science, Part A: Polymer Chemistry,2011,vol. 49,p. 3020 - 3029.
[6]ChemMedChem,2010,vol. 5,p. 65 - 78.

5
[ 515141-52-3 ]
[ 116668-47-4 ]
[ 832102-19-9 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7108 - 7118.

6
5,7-eicosadiynoic acid chloride [ No CAS ]
[ 116668-47-4 ]
[ 870287-80-2 ]

References: [1]Macromolecules,2005,vol. 38,p. 9366 - 9376.

7
4,6-heptadecadiynoic acid chloride [ No CAS ]
[ 116668-47-4 ]
C₂₈H₃₃NO₃ [ No CAS ]

References: [1]Macromolecules,2005,vol. 38,p. 9366 - 9376.

8
[ 116668-47-4 ]
[ 128937-83-7 ]
[ 870287-79-9 ]

References: [1]Macromolecules,2005,vol. 38,p. 9366 - 9376.

9
[ 116668-47-4 ]
[ 832102-21-3 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7108 - 7118.

10
[ 116668-47-4 ]
[ 931088-51-6 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7108 - 7118.

11
[ 116668-47-4 ]
[ 372149-61-6 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7108 - 7118.

12
[ 116668-47-4 ]
[ 832102-22-4 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7108 - 7118.

13
[ 116668-47-4 ]
6-[6-(4-chloro-phenyl)-4-oxo-4<i>H</i>-thieno[3,2-<i>d</i>]pyrimidin-3-yl]-naphthalene-2-carbonyl chloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7108 - 7118.

14
[ 116668-47-4 ]
6-(4-chlorophenyl)-3-[6-(hydroxymethyl)-2-naphthalenyl]thieno[3,2-d]pyrimidin-4(3H)-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7108 - 7118.

15
[ 116668-47-4 ]
6-(4-chlorophenyl)-3-[6-(1-pyrrolidinylcarbonyl)-2-naphthalenyl]thieno[3,2-d]pyrimidin-4(3H)-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7108 - 7118.

16
[ 116668-47-4 ]
6-(4-chlorophenyl)-3-[6-(1-piperidinylmethyl)-2-naphthalenyl]thieno[3,2-d]pyrimidin-4(3H)-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7108 - 7118.

17
[ 116668-47-4 ]
6-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]-N-[2-(1-pyrrolidinyl)ethyl]-2-naphthalenecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7108 - 7118.

18
[ 116668-47-4 ]
6-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]-N-[3-(1-pyrrolidinyl)propyl]-2-naphthalenecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7108 - 7118.

19
[ 116668-47-4 ]
N'-[(6-amino-2-naphthyl)carbonyl]-5-nitro-2-furancarbohydrazide trifluoroacetate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7024 - 7039.

20
[ 116668-47-4 ]
[ 516465-94-4 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7024 - 7039.

21
[ 116668-47-4 ]
(+/-)-(11-hydroxymethyl-8H,16H-7,15-methanodinaphtho[2,1-b][2',1'-f][1,5]-diazocin-3-yl)methanol [ No CAS ]

References: [1]Chemistry - A European Journal,2005,vol. 11,p. 2284 - 2294.

22
[ 116668-47-4 ]
(+/-)-1,1'-diethyl 3,3'-(8H,16H-7,15-methanodinaphtho[2,1-b][2',1'-f][1,5]diazocine-3,11-diyl)dimethylene dimalonate [ No CAS ]

References: [1]Chemistry - A European Journal,2005,vol. 11,p. 2284 - 2294.

23
[ 71590-32-4 ]
[ 116668-47-4 ]

References: [1]Journal of the American Pharmaceutical Association. (Practical pharmacy edition),1952,vol. 41,p. 657 - 658.

24
6-nitro-[2]naphthonitrile [ No CAS ]
[ 116668-47-4 ]

References: [1]Journal of the American Pharmaceutical Association. (Practical pharmacy edition),1952,vol. 41,p. 657 - 658.

25
[ 83008-10-0 ]
[ 116668-47-4 ]

References: [1]Chemische Berichte,1925,vol. 58,p. 1216.

26
[ 116668-47-4 ]
[ 100-44-7 ]
benzyl 6-(benzylamino)-2-naphthoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With potassium carbonate; sodium iodide; In DMF (N,N-dimethyl-formamide); at 80℃;	To a solution (40 [ML)] of 6-amino-2-naphtoic acid [(0.] [500G,] 2.67 mmol) in DMF were added benzyl bromide (1.142 g, 6.68 [MMOL),] potassium carbonate (1. [107 G,] 8.01 mmol) and sodium iodide (1.201 g, 8.01 mmol), and the mixture was stirred at [80°C] overnight. After cooled to room temperature, the mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution. The separated organic phase was washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (hexane: ethyl acetate, 3: 1) to give benzyl 6- [(BENZYLAMINO)-2-NAPHTHOATE] (0.214 g, [21percent)] as a white solid.

References: [1]Patent: WO2003/106402,2003,A1 .Location in patent: Page 54-55.

27
[ 64-17-5 ]
[ 116668-47-4 ]
ethyl 6-aminonaphthalene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		Reference Example 99; ethyl 6-amino-2-naphthoate; [Show Image] 6-Amino-2-naphthoic acid (10.50 g) was suspended in ethanol, thionyl chloride (8.0 mL) was added dropwise thereto, and the mixture was heated under reflux overnight. The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. The residue was dissolved in THF, and the solution was diluted with ethyl acetate, and filtered through NH silica gel (50 g). The filtrate was concentrated under reduced pressure. The residue was crystallized from water, and the crystals were collected by filtration, washed with water, and dried under reduced pressure to give the title compound (16.50 g, yield 70percent) as a brown solid. 1H NMR (300 MHz, CDCl3) delta: 0.31 - 0.46 (m, 2 H) 0.60 - 0.75 (m, 2 H) 1.21 - 1.39 (m, 1 H) 1.45 (t, J=7.06 Hz, 3 H) 3.88 (d, J=6.97 Hz, 2 H) 4.44 (q, J=7.10 Hz, 2 H) 7.00 (d, J=8.85 Hz, 2 H) 7.63 (dd, J=8.85, 2.07 Hz, 1 H) 7.79 - 8.01 (m, 5 H) 8.06 (dd, J=8.48, 1.70 Hz, 1 H) 8.40 (d, J=2.07 Hz, 1 H) 8.56 (s, 1 H).
	With thionyl chloride; for 3h;Heating / reflux;	Z. 1-Chloro-6-fluoro-2-aminonaphthalene To a solution of <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> (1 g, 5.34 MMOL) in ethanol (20 mL), is added dropwise thionyl chloride (0.622 mL, 10.7 MMOL). The resulting reaction solution is heated to reflux temperature under a N2 atmosphere for 3 hours. Concentration and trituration with methanol gives <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> ethyl ester as a brown oil. A mixture of <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> ethyl ester (500 mg, 2.32 MMOL) and nitrosonium tetrafluoroborate (298 mg, 2.56 MMOL) in 1, 2-dichlorobenzene (10 mL) is stirred at room temperature for 12 hours and at 110°C for 1 hour. After cooling to room temperature, the reaction mixture is concentrated by rotary evaporator under high vacuum. The residual oil is purified by flash chromatography on silica gel (DICHLOROMETHANE) to give 6-fluoro-2-naphthoic acid ethyl ester as a yellow oil. To a solution of 6-fluoro-2-naphthoic acid ethyl ester (600 mg, 2.75 MMOL) in ethanol (10 mL) at room temperature, is added 1 N NAOH (2.75 mL, 2.75 MMOL). After stirring at room temperature for 4 hours, water (10 mL) is added. Acidification (2 N HCI) and filtration gives 6-fluoro-2-naphthoic acid as a white solid. To a suspension of 6-fluoro-2-naphthoic acid (450 mg, 2.37 MMOL) and triethylamine (0.66 mL, 4.73 MMOL) in 1,4-dioxane (30 mL) at room temperature, is added DPPA (0.77 mL, 3.55 MMOL). After stirring at room temperature for 2.5 hours, ethanol (1.38 mL, 23.7 MMOL) is added and the reaction is heated to reflux temperature for 12 hours. After cooling to room temperature, the mixture is partitioned between EtOAc and water. The organic layer is washed with brine, dried (NA2SO4) and concentrated by rotary evaporator to give an oil. Flash chromatography on silica gel (3: 1 hexanes/EtOAc) GIVES N- (6-FLUORO-2- naphthyl) carbamic acid ethyl ester as an oil. A mixture of N-(6-fluoro-2-naphthyl) carbamic acid ethyl ester (548 mg, 2.35 MMOL), N-CHLOROSUCCINIMIDE (313 mg, 2.35 MMOL) and 1 M HCI in acetic acid (2.35 mL, 2.35 MMOL) in acetic acid (20 mL) is heated at 50°C under N2 atmosphere for 1 hour. After cooling to room temperature, water (10 mL) is added. The resulting precipitate is removed by filtration to GIVE LS (1-CHLORo-6-FLUORO-2-NAPHTHYL) CARBAMIC acid ethyl ester as a yellow solid. A mixture OF N-(1-CHLORO-6-FLUORO-2-NAPHTHYL) carbamic acid ethyl ester (600 mg, 2.24 MMOL) and KOH (1.51 g, 26.9 MMOL) in ethanol (20 mL) is heated to reflux temperature under N2 atmosphere for 12 hours. After cooling, the reaction mixture is concentrated by rotary evaporator. The residual oil is purified by flash chromatography on silica gel (3: 1 hexanes/EtOAc) to give 1-chloro-6-fluoro-2-aminonaphthalene as a brown solid.

References: [1]ChemMedChem,2015,vol. 10,p. 193 - 206.
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 7256 - 7266.
[3]Patent: EP2261213,2010,A1 .Location in patent: Page/Page column 81.
[4]Patent: WO2004/48314,2004,A1 .Location in patent: Page 44-45.

28
[ 116668-47-4 ]
[ 5042-97-7 ]

Yield	Reaction Conditions	Operation in experiment
		AA. 1, 6-Dichloro-2-aminonaphthalene Sodium nitrite (811 mg, 11.8 MMOL) is added over a period of 15 minutes to concentrated sulfuric acid (10 mL) while stirring. The mixture is heated to 70°C for 15 minutes. After cooling to room temperature, a solution of <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> (2 g, 10.7 MMOL) in acetic acid (10 mL) is added dropwise at such a rate that the temperature is kept below 40°C. After stirring at 40°C for an additional 30 minutes, the reaction mixture is poured into an ice-cooled solution of copper (L) chloride (2.54 g, 25.6 MMOL) in concentrated HCI (30 mL). After stirring at 80°C for 30 minutes, water (80 mL) is added. The precipitate is collected and purified by flash chromatography on silica gel (5percent methanol in DICHLOROMETHANE) to give 6-CHLORO-2-NAPHTHOIC acid as a brown solid. To a suspension of 6-chloro-2-naphthoic acid (1 g, 4.84 MMOL) and triethylamine (1.35 mL, 9.68 MMOL) in 1,4-dioxane (20 mL) at room temperature, is added DPPA (1.56 mL, 7.26 MMOL). After stirring at room temperature for 2.5 hours, ethanol (2.82 mL, 48.4 MMOL) is added and the reaction is heated to reflux temperature for 12 hours. After cooling to room temperature, the mixture is partitioned between EtOAc and water. The organic layer is washed with brine, dried (NA2SO4) and concentrated by rotary evaporator to give an oil. Flash chromatography on silica gel (3: 1 hexanes/EtOAc) gives N- (6-chloro-2- naphthyl) carbamic acid ethyl ester as a white solid. A mixture OF N- (6-CHLORO-2-NAPHTHYL) carbamic acid ethyl ester (725 mg, 2.90 MMOL), N-chlorosuccinimide (387 mg, 2.90 MMOL) and 1 M HCI in acetic acid (2.90 mL, 2.90 MMOL) in acetic acid (20 mL) is heated at 50°C under N2 atmosphere for 1 hour. After cooling to room temperature, water (10 mL) is added and extracted with EtOAc. The organic layer is washed with brine, dried (NA2SO4) and concentrated by rotary evaporator to give N- (1, 6- dichloro-2-naphthyl) carbamic acid ethyl ester as a yellow solid. A mixture OF N- (1, 6-DICHLORO-2-NAPHTHYL) carbamic acid ethyl ester (750 mg, 2.64 MMOL) and KOH (1.78 mg, 31.7 MMOL) in ethanol (20 mL) is heated to reflux temperature-under a N2 atmosphere for 12 hours. After cooling to room temperature, water (10 mL) is added. The resulting precipitation is removed by filtration to give 1, 6-dichloro-2- aminonaphthalene as a solid
		Preparation 33: 6-Chloronaphthalcnc-2-carboxylic acidA stirred solution of <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> (3.14g, 17.0mmol) in water (1OmL) and cone. HCl (2OmL) was cooled to 00C and a solution of sodium nitrite (1.17g.l7.0mmol) in water (1OmL) was added dropwise. After lhr a solution of copper(I)chloride (3.36g, 34.0mmol) in cone. HCl (1OmL) at 00C was added portionwise. The reaction mixture was diluted with water (40OmL) and stirred for 30min. The precipitated solid was collected by filtration, washed several times with water and dried to afford the title compound, deltapi (DMSO): 7.63 (IH, dd), 8.03 (2H, m), 8.17 (2H, m), 8.64 (IH, s).

References: [1]Patent: WO2004/48314,2004,A1 .Location in patent: Page 45-46.
[2]Patent: WO2006/85118,2006,A2 .Location in patent: Page/Page column 29.

29
[ 116668-47-4 ]
C₁₇H₂₃NO₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tert-butyldimethylsilyl chloride; triethylamine; In dichloromethane; for 1h;	Example 20; Synthesis of a compound of Formula (I) where R1, R3, R6, and R(at) are OMe, R(at), R(at), and R10 are Me, R(at) and R5 are OH, R(at) is H, R11 is CN, Y is CH2, and R12 is 6-(5-dimethylaminonaphth-l- ylsulfonylamino)naphth-2-ylcarbonylamino (compound 50); Step 1; To a suspension of <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> (374 mg, 2.0 mmol) in CH2C12 (8 mL) were added TBDMS-Cl (301 mg, 2.0 mmol) and TEA (1.11 mL, 8.0 mmol) in sequence. After stirring for 1 hr, dansyl-chloride (701 mg, 2.6 mmol) was added to the reaction mixture and stirring was continued for an additional 1 hr. The reaction mixture was diluted with CH2Cl2 (50 mL) and IN HCl (aq). separated organic phase was washed with IN HCl (aq) 50 mL) and sat. NaHCO3 (aq) 50 mL) and concentrated in vacuo. The residue was taken up in THF (3 mL) and treated with 2N NaOH(aq) (10 mL) and MeOH (3 mL). After vigorously stirring for 30 min, IN HCI(aq) was added to adjust the pH of the solution to pH -7. The reaction mixture was concentrated in vacuo and the residue was redissolved in CH2C12 (10 mL) and H20 (10 mL). The aqueous layer was extracted with CH2C12 (3x 20 mL). The combined organic layers were dried over Na2S04 and concentrated in vacuo. Precipitation was observed after 3 d and CH2C12 (1 mL) was added to the residue. The precipitation was filtered off and washed with Et20 to afford crude 6-(5-dimethylamino-naphthalene-1-sulfonylamino)-naphthalene-2- carboxylic acid (150 mg, purity 92percent), which was used in the next step without further purification.

References: [1]Patent: WO2005/118584,2005,A2 .Location in patent: Page/Page column 83-84.

30
[ 50-00-0 ]
[ 116668-47-4 ]
[ 5043-05-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium cyanoborohydride; In methanol; water; at 20℃; for 0.5h;	To a solution of <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> (1) (Sigma-Aldrich Japan KK) (90%, 3.00 g, 14.4 mmol) in methanol (120 ml) was added sodium cyanotrihydroborate (3.63 g, 57.7 mmol) and formaldehyde (37% in water, 24 ml), and the reaction mixture was stirred at room temperature for 30 min. After evaporation of the solvent, the residue was extracted with water and chloroform. The aqueous layer was acidified to pH 1 with HCl to give a yellow-ochre solid, and extracted with chloroform. The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated in vacuo to yield compound (2) (3.23 g, quant.) as a yellow-ochre solid; 1H NMR (DMSO-d6) delta 12.63 (brs, 1H), 8.36 (d, 1H, J=1.5 Hz), 7.88 (d, 1H, J=9.2 Hz), 7.78 (dd, 1H, J=1.8, 8.6 Hz), 7.66 (d, 1H, J=9.0 Hz), 7.26 (dd, 1H, J=2.6, 9.2 Hz), 6.94 (d, 1H, J=2.6 Hz), 3.04 (s, 6H); MS (EI) m/z 215 [M+]; HRMS (EI) calculated for C13H13O2N [M+] 215.0946, found 215.0946.
95%	With sodium cyanoborohydride; In methanol; at 0 - 25℃; for 2.16667h;Inert atmosphere;	Sodium cyanoborohydride (588mg, 9.34mmol) was added portion-wise to a mixture of <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> (500mg, 2.67mmol) and formaldehyde (37%, 4.0mL) in methanol (MeOH, 7.0mL) at 0C. After stirring for 10 min at 0C, the mixture was then stirred at room temperature (25C) for 2h. The solvents were removed in vacuo, and the residue was acidified with 1N HCl (aq). Then, the aqueous layer was extracted with ethyl acetate (EtOAc). The collected organic layer was washed with brine, and dried over magnesium sulfate (MgSO4) to afford 6-(N,N-dimethylamino)-2-naphthoic acid 1 (546mg, 95%). The product was used for the next reaction without further purification. 1H NMR (400MHz, DMSO-d6): delta 3.05 (s, 6H), 6.95 (d, J=4.0Hz 1H), 7.26 (dd, J=4.0Hz, 1H), 7.67 (d, J=12.0Hz, 1H), 7.79 (dd, J=4.0Hz, 1H), 7.88 (d, J=12.0Hz, 1H), 8.37 (s, 1H), 12.62 (s, 1H); 13C NMR (400MHz, DMSO-d6): delta 40.4, 105.2, 116.9, 123.6, 125.1, 126.0, 126.2, 130.6, 130.9, 137.5, 150.4, 168.2. HRMS (m/z): [M+H]+calcd. for C13H14NO2, 216.1019; found, 216.1020.

References: [1]Patent: US2006/142311,2006,A1 .Location in patent: Page/Page column 18; sheet 2.
[2]Dyes and Pigments,2019,vol. 171.
[3]Journal of Organic Chemistry,2009,vol. 74,p. 339 - 350.

31
[ 116668-47-4 ]
[ 814-68-6 ]
[ 1089725-57-4 ]

Yield	Reaction Conditions	Operation in experiment
41.5%	With pyridine; In N,N-dimethyl-formamide; at 0 - 20℃; for 2h;	Step-1: 6-Acryloylaminonaphthalene-2-carboxylic acidTo a stirred solution of 2-Amino-6-naphthoic acid (0.3 g, 1.6 mmol) in DMF (2 mL) and pyridine (0.3 mL) was added at 0° C., acryloyl chloride (0.15 g, 1.6 mmol). The resulting mixture was allowed to come to rt and stirred further for 2 h. After that it was poured in water (5 mL) and the solid separated was filtered and dried under reduced pressure to get the desired product (160 mg, 41.5percent) as a pale brown solid. This solid was used in the next step without further purification.

References: [1]Patent: US2008/300268,2008,A1 .Location in patent: Page/Page column 58.

32
C₁₅H₂₀NO₃Pol [ No CAS ]
[ 116668-47-4 ]
C₂₆H₂₇N₂O₄Pol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4068 - 4071.

33
[ 1127736-00-8 ]
[ 116668-47-4 ]
[ 1127736-21-3 ]

Yield	Reaction Conditions	Operation in experiment
		Example 6 6-[({5-[3-Benzyl-8-(trifluoromethyl)quinolin-4-yl]pyridin-3-yl}methyl)amino]-2-naphthoic acid The title compound was prepared from 5-[3-benzyl-8-(trifluoromethyl)quinolin-4-yl]nicotinaldehyde and <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> following the procedure of Example 1 Step 4 as a solid; MS (ES) m/z 564.0.

References: [1]Patent: US2009/69373,2009,A1 .Location in patent: Page/Page column 23.

34
[ 116668-47-4 ]
[ 113239-57-9 ]
[ 1130161-04-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 606 - 609.

35
[ 116668-47-4 ]
[ 6258-06-6 ]
[ 1213268-72-4 ]

Yield	Reaction Conditions	Operation in experiment
	With copper; In aq. phosphate buffer; at 80 - 120℃;pH 6 - 7;Microwave irradiation;	General procedure: Sodium 1-amino-4-ar(alkyl)amino-2-sulfoanthraquinone derivatives were synthesized according to described procedures, using a Cu0-catalyzed microwave-assisted Ullmann-coupling reaction. The following general procedure was applied: A 10 mL microwave vial was charged with bromaminic acid sodium salt (7,0.2?1 mmol) and the respective amine (1.25?3 equiv). A buffer solution of Na2HPO4 (pH 9.6, 4.5 mL) and NaH2PO4 (pH 4.2,0.5 mL) and finely powdered elemental copper (0.002?0.003 g, 5-10 mol percent) were then added. The mixture was irradiated in the microwave oven at 80?120°C for 5-24 min (Scheme 1). After cooling to room temperature, ca. 200 mL of water was added to the filtrate and the aqueous solution was extracted 2?3 times with dichloromethane (200 mL). If needed the organic layer was washed with water and NaOH (0.1 N) to enhance transfer of the product to water. The aqueous layer was then concentrated in vacuo to a volume of 10?20 mL, and subsequently submitted to flash column chromatography using a gradient of acetone in water (5?60percent) as the eluent. Fractions containing blue product were collected. The solvent was evaporated by rotary evaporation to remove acetone and reduce the water volume. Complete removal of water was then achieved by lyophilization using a freeze dryer affording the product as a blue powder. For some compounds the last step of purification (RP-18 flash chromatography) had to be repeated two to three times to obtain pure product (P95percent purity as determined by HPLC-UV (254 nm)-ESI-MS.

References: [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 2076 - 2086.
[2]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4363 - 4371.

Historical Records

Technical Information

• Arndt-Eistert Homologation • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Hunsdiecker-Borodin Reaction • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Passerini Reaction • Petasis Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 116668-47-4

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CAS No.: 116668-47-4

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Product Details of 6-Amino-2-naphthoic acid

Safety of 6-Amino-2-naphthoic acid

Application In Synthesis of 6-Amino-2-naphthoic acid

[ 116668-47-4 ] Synthesis Path-Upstream 1~1

[ 116668-47-4 ] Synthesis Path-Downstream 1~35

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