2-Aminophenol → 3-Benzooxazol-2-yl-phenylamine

HRID 722468Notes

Reaction equation

HRID 722468 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1O.[OH-].[Na+]>>[NH2:1][C:2]1[CH:3]=[C:4]([C:5]2[O:7][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=2)[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 58012-AminophenolHCID 74193-Aminobenzoic AcidHCID 14798Sodium Hydroxide

Product 1

HCID 7209873-Benzooxazol-2-yl-phenylamine

Conditions

Temperature
200 °C

Procedure

3-Aminobenzoic acid (500 mg, 3.65 mmol) and 2-aminophenol (398 mg, 3.65 mmol) were mixed with polyphosphoric acid (5 ml). The reaction was heated to 200° C. for 4 h. The reaction mixture was slowly poured into ice water (100 ml) and the resulting mixture basified with solid sodium hydroxide. At pH5–6 the precipitate was filtered, washed with water and dried to give the subtitle compound, 625 mg (82%). 1H NMR (CDCl3) δ 7.78(m, 1H), 7.65(d, J=7.5 Hz, 1H) 7.59(m, 2H), 7.36(m, 3H), 6.86(dd, J=2.2, 7.9 Hz, 1H). MS 211 m/z (M+H)+.

Workup

  1. filtrationAt pH5–6 the precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-0f7cc6acf6484dc5ab262fffb0da154d
Source dataset
uspto-grants-2006_11
Patent number
US07138425B2

Reaction notes

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