4-Aminobenzoic Acid → 4-(4-Methyl-2-benzoxazolyl)benzenamine

HRID 1401888Notes

Reaction equation

HRID 1401888 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[NH2:11][C:12]1[C:17](O)=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:19]>>[CH3:19][C:13]1[C:12]2[N:11]=[C:6]([C:5]3[CH:4]=[CH:3][C:2]([NH2:1])=[CH:10][CH:9]=3)[O:8][C:17]=2[CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 30141382-Amino-m-cresol

Product 1

HCID 50287054-(4-Methyl-2-benzoxazolyl)benzenamine

Conditions

Temperature
160 °C

Procedure

To a suspension of 4-amino-benzoic acid (2.0 g, 14.5 mmol) in PPA (˜85 g) was added 2-amino-m-cresol (1.8 g, 15.3 mmol). The reaction was heated to 160° C. for 14 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 was subsequently purified by flash column chromatography on silica gel eluting with ethyl acetate in hexanes to afford the desired product, 4-(4-methyl-benzooxazol-2-yl)-phenylamine as a light pink solid, 1.8 g (56%). 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
  6. customwas subsequently purified by flash column chromatography on silica gel eluting with ethyl acetate in hexanes

Sources & evidence

ORD record
ord-5fef8a861f47485e81237a1d3bfa6666
Source dataset
uspto-grants-2014_12
Patent number
US08907103B2

Reaction notes

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