Pyridine → HCID 66621507, compound

HRID 415285Notes

Reaction equation

[NH2:1][C:2]1[C:3]([OH:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=C([C:25]2[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=2)C=1>C1(C)C=CC=CC=1>[OH:12][C:3]1[C:2]([NH:1][C:29](=[O:30])[C:28]2[CH:32]=[CH:33][C:25]([C:16]3[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=3)=[CH:26][CH:27]=2)=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 70 °C

Procedure

Thionyl chloride (10 mL) was added to 4-(pyridin-4-yl)benzoic acid (1.6 g, 8 mmol) and the mixture was stirred under reflux overnight. The solvent was evaporated under reduced pressure and the residue was dried in vacuum giving 4-(pyridin-3-yl)benzoyl chloride. To a solution of methyl 3-amino-2-hydroxybenzoate (1 g, 6 mmol) and pyridine (480 mg, 6 mmol) in toluene (50 mL) was added 4-(pyridin-3-yl)benzoyl chloride (1.3 g, 6 mmol) portion wise at 0° C. and then stirred at 70° C. for 4 h. The resulting mixture was extracted with ethyl acetate (100 mL×4), the organic phase was washed with water and saturated sodium bicarbonate, dried with anhydrous sodium sulfate and evaporated under reduced pressure to obtain methyl 2-hydroxy-3-(4-(pyridin-4-yl)benzamido)benzoate as yellow solid (1.5 g, yield 71%). 1H-NMR (400 MHz, CDCl3) δ 4.00 (s, 3H), 6.97-7.01 (t, J=8.2 Hz, 1H), 7.57-7.63 (m, 3H), 7.78-7.80 (d, J=8.0 Hz, 2H), 8.05-8.07 (d, J=8.8 Hz, 2H), 8.67-8.78 (m, 4H), 11.44 (s, 1H); LC-MS (ESI) m/z: 349 (M+1)+.

Workup

extractionThe resulting mixture was extracted with ethyl acetate (100 mL×4)
washthe organic phase was washed with water and saturated sodium bicarbonate
dry with materialdried with anhydrous sodium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-c4c0010f694c470687fa7b64f97400e1
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088760B2

Reaction notes

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