Acetic Acid → 2-Methyl-1,3-benzoxazole-6-carboxylic acid

HRID 1393687Notes

Reaction equation

HRID 1393687 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].[C:12](O)(=O)[CH3:13]>>[CH3:12][C:13]1[O:11][C:3]2[CH:4]=[C:5]([C:6]([OH:8])=[O:7])[CH:9]=[CH:10][C:2]=2[N:1]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 1375664-Amino-3-hydroxybenzoic acid

Product 1

HCID 184756892-Methyl-1,3-benzoxazole-6-carboxylic acidYield 62%

Conditions

Temperature
130 °C

Procedure

4-Amino-3-hydroxybenzoic acid (4.9 g) was added to acetic acid (250 ml) and stirred for 3 days at 130° C. The solution was concentrated under reduced pressure, and precipitates were collected by filtration. The precipitates were dissolved in methanol and chloroform. The solution was concentrated under reduced pressure, and precipitates were collected by filtration, washed with methanol and dried under reduced pressure to give the title compound (3.5 g, Y.:62%).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customprecipitates
  3. filtrationwere collected by filtration
  4. dissolutionThe precipitates were dissolved in methanol
  5. concentrationThe solution was concentrated under reduced pressure
  6. customprecipitates
  7. filtrationwere collected by filtration
  8. washwashed with methanol
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-e58786c4906c46e8bced78b68724e142
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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