610-37-7|5-Hydroxy-2-nitrobenzoic acid| Ambeed

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Quality Control of [ 610-37-7 ] Purity: 98% SDS Specification

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Product Details of [ 610-37-7 ]

CAS No. :	610-37-7
Formula :	C₇H₅NO₅
M.W :	183.12
SMILES Code :	OC(=O)C1=C(C=CC(O)=C1)[N+]([O-])=O
MDL No. :	MFCD00017566
Boiling Point :	No data available
InChI Key :	BUHKQTKKZAXSMH-UHFFFAOYSA-N
Pubchem ID :	11882

Safety of [ 610-37-7 ]

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

Computational Chemistry of [ 610-37-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	5.0
Num. H-bond donors	2.0
Molar Refractivity	44.25
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	103.35 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	-0.1
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.15
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.0
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.04
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.38
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.13

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.91
Solubility	2.26 mg/ml ; 0.0123 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.91
Solubility	0.223 mg/ml ; 0.00122 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.58
Solubility	48.5 mg/ml ; 0.265 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.6 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	2.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.69

Application In Synthesis of [ 610-37-7 ]

* 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.

Downstream synthetic route of [ 610-37-7 ]

[ 610-37-7 ] Synthesis Path-Downstream 1~35

1
[ 623-11-0 ]
[ 610-28-6 ]
[ 610-37-7 ]
[ 96-97-9 ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 1633.

2
[ 42454-06-8 ]
[ 610-37-7 ]

References: [1]Tetrahedron,2002,vol. 58,p. 8107 - 8111.
[2]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1957,vol. 308,p. 51,55.
[3]Journal of the American Chemical Society,1980,vol. 102,p. 6586 - 6587.

3
[ 99-06-9 ]
[ 610-37-7 ]
[ 619-14-7 ]
[ 54797-73-8 ]
[ 67175-28-4 ]

References: [1]Journal of the Chinese Chemical Society,2005,vol. 52,p. 581 - 588.

4
[ 394-31-0 ]
[ 610-37-7 ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 17578 - 17579.

5
[ 610-37-7 ]
5-[2-(2,4-dichloro-phenyl)-ethoxy]-2-nitro-benzoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3290 - 3312.

6
[ 610-37-7 ]
5-[2-(2,4-dichloro-phenyl)-ethoxy]-2-nitro-benzoic acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3290 - 3312.

7
[ 610-37-7 ]
5-[2-(2,4-dichloro-phenyl)-ethoxy]-2-nitro-N-(3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-ylmethyl)-benzamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3290 - 3312.

8
[ 610-37-7 ]
2-amino-N-(4-chloro-phenyl)-5-hydroxy-benzamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 507 - 511.

9
[ 610-37-7 ]
N-(4-chloro-phenyl)-5-hydroxy-2-nitro-benzamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 507 - 511.

10
[ 610-37-7 ]
3-chloro-benzo[b]thiophene-2-carboxylic acid [2-(4-chloro-phenylcarbamoyl)-4-hydroxy-phenyl]-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 507 - 511.

11
[ 610-37-7 ]
[ 499973-05-6 ]

References: [1]Tetrahedron,2002,vol. 58,p. 8107 - 8111.

12
[ 610-37-7 ]
2-nitro-5-prop-2-ynyloxy-benzoyl chloride [ No CAS ]

References: [1]Tetrahedron,2002,vol. 58,p. 8107 - 8111.

13
[ 610-37-7 ]
[ 499973-04-5 ]

References: [1]Tetrahedron,2002,vol. 58,p. 8107 - 8111.

14
[ 610-37-7 ]
(S)-1-(2-Amino-5-propoxy-benzoyl)-pyrrolidine-2-carboxylic acid methyl ester [ No CAS ]

References: [1]Tetrahedron,2002,vol. 58,p. 8107 - 8111.

15
[ 610-37-7 ]
[ 499973-06-7 ]

References: [1]Tetrahedron,2002,vol. 58,p. 8107 - 8111.

16
[ 610-37-7 ]
[ 17730-74-4 ]

References: [1]Journal of the Chemical Society,1921,vol. 119,p. 1431.

17
[ 610-37-7 ]
[ 108129-56-2 ]

References: [1]Journal of the Chemical Society,1921,vol. 119,p. 1431.

18
[ 2516-95-2 ]
[ 610-37-7 ]

Yield	Reaction Conditions	Operation in experiment
96.5%	With sodium hydroxide; In water; for 72.0h;Inert atmosphere;	5-Chloro-2-nitrobenzoic acid (32.00 g, 0.159 mol),Dissolved in 15% aqueous sodium hydroxide solution,The reaction was refluxed under N2 for 72h.After completion of the reaction, the pH of the solution was adjusted to 1.0, extracted with ethyl acetate, the combined ethyl acetate layers were dried over anhydrous sodium sulfate,The solvent was distilled off under reduced pressure to give 28.05 g of 5-hydroxy-2-nitrobenzoic acid in a yield of 96.5%.
90%	With potassium hydroxide; In water; for 24.0h;Reflux;	Step 1: (0332) Potassium hydroxide aqueous solution (13.8 g, 248 mmol, 40 ml) was added into 5-chloro-2-nitrobenzoic acid 11-a (5 g, 24.8 mmol) and the mixture was stirred at reflux for 24 hours. The pH value of the reaction mixture was adjusted to 2 with concentrated hydrochloric acid under ice-cooling, the precipitated solid was filtered and dried to give 11-b as a white solid (4.1 g, yield: 90%).
	With sodium hydroxide; In water; for 18.0h;Heating / reflux;	124.6 g (0.618 mol) of 5-chloro-2-nitro-benzoic acid (Fluka Buchs, Switzerland) are heated under reflux in an aqueous sodium hydroxide solution [197.8 g (4.94 mol) of NaOH in 1. 231 water] for 18 h. The cold reaction mixture is extracted several times with ether-ethyl acetate, washed with brine and dried over sodium sulfate. The raw material is crystallized from iso- propyl ether-hexane. The crystals are filtered off and dried at 50C (high-vacuum). mp: 167- 171 C ; MS: 182 (M+-1) ; HPLC: tut=6. 315 min (Grad 1).

	With hydrogenchloride; sodium hydroxide; In water;	EXAMPLE 45 Preparation of 5-hydroxy-2-nitrobenzoic acid A mixture of 5.0 l. of water, 800 g. of sodium hydroxide and 504 g. of 5-chloro-2-nitrobenzoic acid was refluxed for 24 hours. The solution was cooled and acidified with 1.75 l. of concentrated hydrochloric acid. The acidic aqueous mixture was extracted three times with 1.5 l. of ether. The combined ether extracts were dried over anhydrous magnesium sulfate, filtered through Celite and evaporated to a light yellow solid (473 g.). This material was recrystallized from ether-petroleum ether to yield 298 g. of 5-hydroxy-2-nitrobenzoic acid, mp 167-169 (65.2%).
	With potassium hydroxide; potassium hydrogencarbonate; In water; dimethyl sulfoxide;	Step 1. 5-Hydroxy-2-nitrobenzoic acid. 5-Chloro-2-nitrobenzoic acid (100 g) in 800 ml dimethylsulfoxide was treated with 112 g powdered KOH with cooling, 170 ml anhydrous alcohol added and the mixture stirred 2 hours at 25 and then left overnight. The mixture was kept at 28 for about 8 hours, then overnight at 0, warmed to room temperature and 3.5 liters of water added. The mixture was acidified with HCl, 1 kg NaCl added and extracted with ethyl acetate. The extract was washed with water, dried, 50 g KHCO3 in 500 ml water added, diluted to 2 liters, and the ethyl acetate blown off with a stream of nitrogen. The solution was acidified and filtered to give 56 g product, m.128-30.

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 14654 - 14664.
[2]Patent: CN106478548,2017,A .Location in patent: Paragraph 0019-0020; 0035-0036; 0051-0052; 0067-0068.
[3]Patent: US2017/158680,2017,A1 .Location in patent: Paragraph 0330; 0331; 0332.
[4]Patent: WO2003/97641,2003,A2 .Location in patent: Page/Page column 63.
[5]Patent: US4348396,1982,A .
[6]Patent: US4205173,1980,A .

19
[ 64-17-5 ]
[ 610-37-7 ]
[ 452077-39-3 ]

Yield	Reaction Conditions	Operation in experiment
92.8%	With sulfuric acid; for 12.0h;Cooling with ice; Reflux;	5-Hydroxy-2-nitrobenzoic acid (21.58 g, 0.118 mol) was dissolved in ethanol in a 1000 ml single-necked flask andconcentrated sulfuric acid (23.11 g, 0.236 mol) was added dropwise in anice bathand refluxed for 12 h.The reaction was completed, the reaction solution was poured into the ice solid precipitation, suction filtration, the filter cake collected 5-hydroxy-2-nitrobenzoate 23.09g, yield 92.8%.

References: [1]Patent: CN106478548,2017,A .Location in patent: Paragraph 0069-0070; 0101-0102.
[2]Patent: WO2004/39764,2004,A1 .Location in patent: Page/Page column 102.

20
[ 610-37-7 ]
[ 59216-77-2 ]

Yield	Reaction Conditions	Operation in experiment
52%	With sulfuric acid; magnesium sulfate; In methanol;	Step 1 Methyl 5-hydroxy-2-nitrobenzoate To a stirred suspension of <strong>[610-37-7]5-hydroxy-2-nitrobenzoic acid</strong> (5.1 g, 28 mmol) in methanol (20 ml) was added sulfuric acid (95%, 8 ml) at room temperature. The solution was stirred at 90 C. for 1 hour after which it was allowed to reach room temperature and carefully poured into saturated sodium bicarbonate. Subsequent extraction with dichloromethane, drying of the organic phase using magnesium sulfate and concentration in vacuo gave the title compound (2.8 g, 52%) as a yellow solid. 1H NMR (DMSO) delta 11.40 (br s, 1H), 8.04 (d, J=8.97 Hz 1H), 7.05-6.98 (m, 2H), 3.82 (s, 3H); MS m/z (M-1) 196.

References: [1]Patent: US2003/73862,2003,A1 .

21
[ 855719-15-2 ]
aquo-dichloro-tin(II) [ No CAS ]
[ 610-37-7 ]
[ 81156-68-5 ]
[ 335440-02-3 ]

Yield	Reaction Conditions	Operation in experiment
	With N-benzyl-trimethylammonium hydroxide; diisopropyl (E)-azodicarboxylate; triphenylphosphine;benzotriazol-1-ol; In tetrahydrofuran; N,N-dimethyl-formamide;	Example 7 (S)-2-Amino-N-(1-carbamoyl-4-guanidino-butyl)-5-[2-(2,4-dichlorophenyl)ethoxy]benzamide Rink resin (306 mg; loading 0.43 mmol/g) functionalized with Arg(Boc)2 was coupled with 146 mg of <strong>[610-37-7]5-hydroxy-2-nitrobenzoic acid</strong> in the presence of DIC (136 mg) and HOBt (140 mg) in DMF (2 ml) for 3 h at room temperature. The resin was then washed and treated with a 15% solution of benzyltrimethylammonium hydroxide in DMF for 60 min. The resin was washed with DMF, 10% acetic acid in DMF, DMF and DCM and dried in vacuo for 4 h. The dried resin was washed with anhydrous THF and mixed with 534 mg (2 mmol) of triphenylphosphane, 422 mg (2 mmol) of 2-(2,4-dichlorophenyl)ethanol and 400 mul (2 mmol) of DIAD in dry THF. The mixture was kept overnight at room temperature. The resin was washed and treated with 415 mg of tin dichloride monohydrate in 2 ml of DMF and 0.5 ml of trifluoroethanol. The reduction was continued overnight at room temperature. The resin was washed and dried, and the final product was cleaved off and processed as described in Example 1. MS: 481 (M+H)+

References: [1]Patent: US6472562,2002,B1 .

22
[ 610-37-7 ]
[ 100-39-0 ]
[ 61340-14-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate; In N,N-dimethyl-formamide; at 10 - 35℃; for 15.0h;	Step 1 To a solution of <strong>[610-37-7]5-hydroxy-2-nitrobenzoic acid</strong> (10.0 g, 54.6 mmol) in DMF (200 mL) were added benzylbromide (20.5 g, 120 mmol) and potassium carbonate (18.9 g, 137 mmol), and the mixture was stirred at room temperature for 15 hrs. The reaction mixture was concentrated under reduced pressure and water was added to the concentrated residue. The precipitated insoluble material was collected by filtration and the solid was washed with water to give benzyl 5-benzyloxy-2-nitrobenzoate as a yellow powder (19.4 g, 98%).
89%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	Compound 5A (1.33 g, 7.26 mmol), benzyl bromide (2.73 g, 16.0 mmol), and Cs2CO3 (7.1 g, 22.0 mmol) were mixed in DIVJF (30 ml) and stirred at room temperature overnight. Saturated aqueous NaHCO3 (100 ml) was added and the aqueous phase was extracted with EtOAc (100 mL) twice. The combined organic phases were washed with brine (50 ml), dried over Na2SO4, filtered, and concentrated by rotary evaporator. The product was isolated by silica gel chromatography (Hexane/EtOAc: 10:1 to 5:1) to give compound 5B (2.25 g, 89%).

References: [1]Patent: US2015/329556,2015,A1 .Location in patent: Paragraph 1564.
[2]Patent: WO2006/19768,2006,A1 .Location in patent: Page column 84.

23
[ 610-37-7 ]
dipotassium salt of 5-hydroxy-2-nitrobenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In methanol;	EXAMPLE 10 To a solution of 10 parts of <strong>[610-37-7]5-hydroxy-2-nitrobenzoic acid</strong> in 320 parts of methanol, was added 6.1 parts of potassium hydroxide. The mixture was allowed to react under ambient conditions for about one hour. The resulting dipotassium salt of <strong>[610-37-7]5-hydroxy-2-nitrobenzoic acid</strong> was dried by removing the solvent under reduced pressure. The dipotassium salt was then combined with 380 parts of sulfolane; 310 parts of N-methyl-2-pyrrolidone; and 50 parts of 3-chloro-4-fluorobenzotrifluoride.
	With potassium hydroxide; In methanol;	EXAMPLE 10 To a solution of 10 parts of <strong>[610-37-7]5-hydroxy-2-nitrobenzoic acid</strong> in 320 parts of methanol, was added 6.1 parts of potassium hydroxide. The mixture was allowed to react under ambient conditions for about one hour. The resulting dipotassium salt of <strong>[610-37-7]5-hydroxy-2-nitrobenzoic acid</strong> was dried by removing the solvent under reduced pressure. The di-potassium salt was then combined with 380 parts of sulfolane; 310 parts of N-methyl-2-pyrrolidone; and 50 parts of 3-chloro-4-fluorobenzotrifluoride.

References: [1]Patent: US4603222,1986,A .
[2]Patent: US4469893,1984,A .

24
[ 610-37-7 ]
[ 75-26-3 ]
[ 68701-49-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N-methyl-acetamide;	EXAMPLE 46 Preparation of 5-isopropoxy-2-nitrobenzoic acid, isopropyl ester A mixture of 55.3 g. of <strong>[610-37-7]5-hydroxy-2-nitrobenzoic acid</strong>, 450 ml. of dimethylformamide and 93.9 g. of anhydrous potassium carbonate was stirred at room temperature for 10 minutes. 100 Ml. of isopropylbromide was then added and the mixture was stirred and heated to 100 for five hours. The reaction mixture was then cooled and diluted with ice water. The pH of the mixture was adjusted to ~8 with 4 N sodium hydroxide solution. The mixture was then extracted three times with 500 ml. of ether. The combined ether extracts were washed with 500 ml. of saturated brine, dried over anhydrous potassium carbonate, filtered through Celite and evaporated to a yellow oil which crystallized on cooling to yield 74.0 g. of 5-isopropoxy-2-nitrobenzoic acid, isopropyl ester, mp 45-50 (91.7%). This material may be distilled under high vacuum to give pure product, mp 51-52.

References: [1]Patent: US4348396,1982,A .

25
BF₃ -ether [ No CAS ]
[ 610-37-7 ]
[ 59216-77-2 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; water;	Step 2. Methyl 5-hydroxy-2-nitrobenzoate. 5-Hydroxy-2-nitrobenzoic acid (47 g) in 750 ml methanol was treated with 160 ml BF3 -ether, ether distilled off until pot temperature reached 60, and refluxed overnight. The procedure was repeated with 100 ml BF3 -ether. The mixture was poured into 3 volumes of water, extracted with ethyl acetate, the ethyl acetate washed with water, KHCO3 solution, water, dried and concentrated to give 48.4 g product.

References: [1]Patent: US4205173,1980,A .

26
[ 610-37-7 ]
allyl 5-allyloxy-2-nitrobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The starting materials were prepared as follows: 5-Hydroxy-2-nitrobenzoic acid was allylated using the method described in example 1 except using <strong>[610-37-7]5-hydroxy-2-nitrobenzoic acid</strong> in place of 3-hydroxy-4-nitrobenzoic acid, to give allyl 5-allyloxy-2-nitrobenzoate. NMR (DMSO-d6): delta 4.78 (t, 4H); 5.27-5.48 (m, 4H); 5.91-6.13 (m, 2H); 7.29 (m, 2H); 8.13 (d, 1H).

References: [1]Patent: US5541178,1996,A .

27
[ 610-37-7 ]
[ 107-07-3 ]
[ 849421-50-7 ]

Yield	Reaction Conditions	Operation in experiment
68%		5-hydro-2-nitro-benzoic acid of formula 36 (1.83 g, 10 mmol) is dissolved in tetrahydrofuran (50 ml); 2-chloroethanol (20 mmol) and triphenylphosphine (20 mmol) are added. To the solution, diethylazodicarboxylate (20 mmol) is added slowly. The reaction is stirred for 1 hour. 10 mmol more of 2- CHLOROETHANOL, triphenylphosphine and diethylazodicarboxylate are added sequentially. The reaction is stirred at room temperature overnight. To the reaction, IN sodium hydroxide (50 ml) is added and stirred for 2 hours. The mixture is diluted with water (100 ml) and extracted with dichloromethane three times (3X20 ml). The aqueous layer is filtered by suction and washed with water and the filtrate is acidified using concentrated hydrochloric acid to pH = 2-3. The precipitate is filtered by suction and washed with water and dried under vacuum. 1.67 g (68%) of compound of formula 37 is obtained.

References: [1]Patent: WO2005/30131,2005,A2 .Location in patent: Page/Page column 32.

28
[ 610-37-7 ]
[ 75-65-0 ]
[ 117207-68-8 ]

References: [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 6659 - 6670.

29
[ 610-37-7 ]
[ 1007374-52-8 ]

References: [1]Patent: US2008/45516,2008,A1 .

30
[ 610-37-7 ]
[ 1276040-19-7 ]