Methanol → 2-Phenylaminobenzoxazol-6-acetic acid

HRID 1372556Notes

Reaction equation

HRID 1372556 reaction equation
CO.[C:3]1([NH:9][C:10]2[O:11][C:12]3[CH:18]=[C:17]([CH2:19][C:20]([O:22]C)=[O:21])[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>O1CCCC1>[C:3]1([NH:9][C:10]2[O:11][C:12]3[CH:18]=[C:17]([CH2:19][C:20]([OH:22])=[O:21])[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 17859442Methyl 2-phenylaminobenzoxazol-6-acetate

Product 1

HCID 111498372-Phenylaminobenzoxazol-6-acetic acidYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In tetrahydrofuran (which will hereinafter be abbreviated as “THF”) (2 ml) and methanol (2 ml) was dissolved methyl 2-phenylaminobenzoxazol-6-acetate (460 mg, 1.63 mmol), followed by the addition of 1N NaOH (3.3 ml) under stirring at room temperature. After further stirring overnight at room temperature, the reaction mixture was concentrated into a small volume. The concentrate was acidified with acetic acid. The crystals thus obtained were collected by filtration, washed with water and then dried, whereby 2-phenylaminobenzoxazol-6-acetic acid (348 mg, 80%) was obtained as a pale yellow solid.

Workup

  1. stirringAfter further stirring overnight at room temperature
  2. concentrationthe reaction mixture was concentrated into a small volume
  3. customThe crystals thus obtained
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-2e472908fbcb4426980961c22984f323
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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