Pyridine → HCID 66620856, compound

HRID 415146Notes

Reaction equation

HRID 415146 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.[F:19][C:20]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23]>C1(C)C=CC=CC=1>[F:19][C:20]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[CH:26]=[CH:25][C:21]=1[C:22]([NH: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])=[O:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12782444Methyl 3-amino-2-hydroxybenzoateHCID 86633085HCID 86633085, compound

Product 1

HCID 66620856HCID 66620856, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 3-amino-2-hydroxybenzoate (1.42 g, 8.50 mmol) and pyridine (1.0 mL, 8.5 mmol) in toluene (20 ml) was added 2-fluoro-4-(pyridine-2-yl)benzoyl chloride (2.0 g, 8.50 mmol) portion wise at 0° C. and then stirred at 70° C. for 4 h. The resulting mixture was extracted with ethyl acetate (4×100 mL). The organic phase was washed with water and saturated sodium bicarbonate, dried with anhydrous sodium sulfate and evaporated under reduced pressure to obtain methyl 3-(2-fluoro-4-(pyridin-2-yl)benzamido)-2-hydroxybenzoate as a yellow solid (1.40 g, yield 45%). LC-MS (ESI) m/z: 367 (M+1)+.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (4×100 mL)
  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-43309d6a68654121b029900573881b49
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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