p-Toluenesulfonic acid → 2-Methyl-1,3-benzoxazole-7-carboxylic acid

HRID 2064768Notes

Reaction equation

HRID 2064768 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].[CH3:12][C:13]1C=CC(S(O)(=O)=O)=CC=1>C(OCC)(OCC)(OCC)C>[CH3:12][C:13]1[O:11][C:3]2[C:4]([C:5]([OH:7])=[O:6])=[CH:8][CH:9]=[CH:10][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 684433-Aminosalicylic acid

Product 1

HCID 5947092-Methyl-1,3-benzoxazole-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 66221Triethyl orthoacetateSolvent

Procedure

A solution of 3-amino-2-hydroxy-benzoic acid (9.40 mmol) and PTSA (0.34 mmol) in triethyl orthoacetate (5.77 mL) is heated to reflux for 5 h and concentrated in vacuo. The residue is washed with ether and dried in vacuo to give the desired product which is used without further purification. LC-MS: tR=0.67 min; [M+H]+=178.0.

Workup

  1. temperatureto reflux for 5 h
  2. concentrationconcentrated in vacuo
  3. washThe residue is washed with ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-039a048575804c22911b85f49923fe94
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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