Formic Acid → Anthranil
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH:9]([OH:11])=[O:10]>>[CH:9]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8])=[O:10].[N:1]1[O:11][CH:9]=[C:3]2[C:2]=1[CH:7]=[CH:6][CH:5]=[CH:4]2.[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]=[O:10]Participants
5
Procedure
2-Formamidophenol (m.p. 129° C.) is prepared by heating 2-aminophenol and formic acid (E. Bamberger, Chem. Ber., 1903, 36, p. 2052) and is formed together with anthranil by the oxidation of 2-aminobenzaldehyde with neutral permonosulfuric acid. 2-Acetamidophenol (m.p. 201° C.) is formed by the regulated acetylation of 2-aminophenol, by dissolving 2-acetamidophenol in caustic soda solution (Bamberger, loc. cit.) or by the reduction of 2-nitrophenol with tin and acetic acid (J. B. Tingle and L. F. Williams, Amer. Chem. J., 1907, 37, p. 57).
Sources & evidence
- ORD record
- ord-b3a213ac84f443f6b14fac79185ea679
- Source dataset
- uspto-grants-1985_05
- Patent number
- US04517005
Reaction notes
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