2-Aminophenol → HCID 61827628, compound

HRID 2371296Notes

Reaction equation

HRID 2371296 reaction equation
C([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[C:7]([CH3:14])[CH:6]=1)(=O)C.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1O>>[O:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:9]1[C:8]1[CH:12]=[CH:13][C:5]([NH2:4])=[CH:6][C:7]=1[CH3:14]

Participants

3

Reactant 2

HCID 58012-AminophenolHCID 27352244-Acetamido-2-methylbenzoic acid

Product 1

HCID 61827628HCID 61827628, compound

Conditions

Temperature
200 °C

Procedure

To a suspension of 4-acetylamino-2-methyl-benzoic acid (2.0 g, 10.3 mmol) in PPA (˜85 g) was added aminophenol (1.2 g, 10.8 mmol). The reaction was heated to 200° C. for 2 h, then carefully quenched in aqueous sodium carbonate (˜50% saturated) at room temperature. Ethyl acetate was added, and the organic layer was washed with water and brine, and dried over sodium sulfate. The crude product was obtained as an orange oil and was subsequently purified by flash column chromatography on silica gel eluting with ethyl acetate in hexanes to afford the desired product, 4-benzooxazol-2-yl-3-methyl-phenylamine as a colorless solid, 290 mg (13%). 1H NMR (300 MHz, DMSO-d6): δ 7.84-7.81 (m, 1H), 7.64-7.62 (m, 2H), 7.32-7.27 (m, 2H), 6.51 (d, J=9.0 Hz, 2H), 5.83 (s, 2H), 2.61 (s, 3H). LC-MS m/z=225 [C14H12N2O+H]+.

Workup

  1. customcarefully quenched in aqueous sodium carbonate (˜50% saturated) at room temperature
  2. additionEthyl acetate was added
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe crude product was obtained as an orange oil
  6. customwas subsequently purified by flash column chromatography on silica gel eluting with ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7108ff430c434b28ad595d87a89ef173
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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