p-Toluenesulfonic acid monohydrate → Methyl 2-(3-(pyridin-3-yl)phenyl)benzo[d]oxazole-7-carboxylate

HRID 415298Notes

Reaction equation

HRID 415298 reaction equation
O[C:2]1[C:11]([NH:12][C:13](=[O:26])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[CH:15]=2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].O.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:16]2[CH:15]=[C:14]([C:13]3[O:26][C:2]4[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[CH:10][C:11]=4[N:12]=3)[CH:19]=[CH:18][CH:17]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 66620659Methyl 2-hydroxy-3-(3-(pyridin-3-yl)benzamido)benzoate

Product 1

HCID 66620321Methyl 2-(3-(pyridin-3-yl)phenyl)benzo[d]oxazole-7-carboxylateYield 15.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 2-hydroxy-3-(3-(pyridin-3-yl)benzamido)benzoate (0.9 g, 2.5 mmol) and 4-methylbenzenesulfonic acid monohydrate (1 g, 5 mmol) were added to toluene (20 mL) and the mixture was stirred under reflux for 2 days. The resulting mixture was extracted with ethyl acetate (100 mL×4) and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 10:1). 130 mg of methyl 2-(3-(pyridin-3-yl)phenyl)benzo[d]oxazole-7-carboxylate as a solid was obtained. Yield: 15%. LC-MS (ESI) m/z: 331 (M+1)+.

Workup

  1. temperatureunder reflux for 2 days
  2. extractionThe resulting mixture was extracted with ethyl acetate (100 mL×4)
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 10:1)

Sources & evidence

ORD record
ord-f9b7e43aef4448478c1e43cdb0fc0353
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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