p-Toluenesulfonic acid → HCID 66621160, compound

HRID 415229Notes

Reaction equation

HRID 415229 reaction equation
O[C:2]1[C:11]([NH:12][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:13]2[O:20][C:2]3[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[CH:10][C:11]=3[N:12]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 66620739HCID 66620739, compound

Product 1

HCID 66621160HCID 66621160, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 2-hydroxy-3-(nicotinamido)benzoate (215 mg, 0.79 mmol) and 4-methylbenzenesulfonic acid (400 mg, 2.0 mmol) were added to toluene (10 mL) and the mixture was stirred at reflux for 10 hr. The resulting mixture was extracted with ethyl acetate (100 mL×4) and concentrated to obtain methyl 2-(pyridin-3-yl)benzo[d]oxazole-7-carboxylate as a solid (135 mg, yield 67%); LC-MS (ESI) m/z 255 [M+1]+.

Workup

  1. temperatureat reflux for 10 hr
  2. extractionThe resulting mixture was extracted with ethyl acetate (100 mL×4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0bd53ed6a10b40659b4144db4dd052fc
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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