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Pyridine → Methyl 2-hydroxy-3-(4-(pyridin-2-yl)benzamido)benzoate

HRID 415275
Notes
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Reaction equation

HRID 415275 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].N1C=CC=CC=1.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=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:20]3[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=3)=[CH:26][CH:27]=2)=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 120170524-(2-Pyridinyl)benzoyl ChlorideHCID 12782444Methyl 3-amino-2-hydroxybenzoate

Product 1

HCID 66621294Methyl 2-hydroxy-3-(4-(pyridin-2-yl)benzamido)benzoateYield 76.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Thionyl chloride (10 mL) was added to 4-(pyridin-2-yl)benzoic acid (1.8 g, 9 mmol) and the mixture was stirred under reflux overnight. The solvent was evaporated under reduced pressure and the residue was dried in vacuum to give crude 4-(pyridin-2-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) were added the crude 4-(pyridin-2-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 yellow solid of methyl 2-hydroxy-3-(4-(pyridin-2-yl)benzamido)benzoate (1.6 g, yield 76%). LC-MS (ESI) m/z: 349 (M+1)+. (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-463ae14253cc47c8a47dbb9ef3836528
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08088760B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes