Ethyl orthoformate → 2-(1,3-Benzoxazol-5-yl)acetic acid

HRID 1443829Notes

Reaction equation

HRID 1443829 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[CH:13](OCC)(OCC)OCC>C1(C)C=CC=CC=1>[O:8]1[C:7]2[CH:6]=[CH:5][C:4]([CH2:9][C:10]([OH:12])=[O:11])=[CH:3][C:2]=2[N:1]=[CH:13]1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 1473103(3-Amino-4-hydroxyphenyl)acetic acid

Product 1

HCID 14731072-(1,3-Benzoxazol-5-yl)acetic acidYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The mixture of (3-amino-4-hydroxy-phenyl)-acetic acid (250 mg, 1.5 mmol) and triethyl orthoformate (30 mg, 2.0 mmol) in toluene was refluxed for 3 h, cooled to room temperature and concentrated. The resulting solid was collected, washed with 1:3 ethyl acetate:hexane and dried to give the title compound (220 mg, 83%). 1H NMR (400 MHz, DMSO) δ 12.4 (b s, 1H), 8.70 (s, 1H), 7.68 (d, J=6.7 Hz, 1H), 7.66 (s, 1H), 7.31 (d, J=6.8 Hz, 1H), 3.33 (s, 2H). Mass spectrum (LCMS, ESI pos.): Calcd for C9H7NO3: 177.2. Found: 178.2 (M+H).

Workup

  1. temperaturewas refluxed for 3 h
  2. concentrationconcentrated
  3. customThe resulting solid was collected
  4. washwashed with 1:3 ethyl acetate
  5. dry with materialhexane and dried

Sources & evidence

ORD record
ord-c5fadbe18682442f8fb1111aee5aeb3e
Source dataset
uspto-grants-2010_02
Patent number
US07662824B2

Reaction notes

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