p-Toluenesulfonic acid → Ethyl 2-methylbenzo[d]oxazole-7-carboxylate

HRID 445874Notes

Reaction equation

HRID 445874 reaction equation
[NH2:1][C:2]1[C:3]([OH:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH2:12](C(CC)(CC)C([O-])([O-])[O-])[CH3:13].[CH3:23][C:24]1C=CC(S(O)(=O)=O)=CC=1>>[CH3:12][C:13]1[O:11][C:3]2[C:4]([C:5]([O:7][CH2:23][CH3:24])=[O:6])=[CH:8][CH:9]=[CH:10][C:2]=2[N:1]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 684433-Aminosalicylic acidHCID 21875354Triethylorthoaceate

Product 1

HCID 12157468Ethyl 2-methylbenzo[d]oxazole-7-carboxylateYield 95%

Procedure

A solution of 3-amino-2-hydroxybenzoic acid (1 g, 6.53 mmol), triethylorthoacetate (4 mL), and P-toluenesulfonic acid (40 mg) was heated at 100° C. for 18 hours. The reaction was concentrated in vacuo and the crude product was purified by flash column chromatography on silica gel with hexanes and EtOAc (30%) to afford ethyl 2-methylbenzo[d]oxazole-7-carboxylate (743) (1.27 g, 95%).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe crude product was purified by flash column chromatography on silica gel with hexanes and EtOAc (30%)

Sources & evidence

ORD record
ord-d01bd0af203a435688dbcd32d6d018ab
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

Loading…