3-Aminosalicylic acid → 2-Methyl-1,3-benzoxazole-7-carboxylic acid

HRID 560307Notes

Reaction equation

HRID 560307 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].O.[C:13]1(C)C=CC(S(O)(=O)=O)=C[CH:14]=1>C(OCC)(OCC)(OCC)C>[CH3:13][C:14]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 684433-Aminosalicylic acidHCID 521998p-Toluenesulfonic acid monohydrate

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 p-toluenesulfonic acid monohydrate (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.

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-db5c1c6d4ac541c791bfaf6e98de450c
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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