4-Amino-3-fluorophenol → 2-Amino-5-hydroxybenzamide

HRID 658462Notes

Reaction equation

HRID 658462 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:18]([O-])=O)=[C:13]([CH:17]=1)[C:14]([NH2:16])=[O:15])C1C=CC=CC=1.NC1C=CC(O)=CC=1F>>[NH2:18][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:17][C:13]=1[C:14]([NH2:16])=[O:15]

Participants

3

Reactant 2

HCID 27359194-Amino-3-fluorophenolHCID 599875215-Benzyloxy-2-nitrobenzamide

Product 1

HCID 120149202-Amino-5-hydroxybenzamideYield 99%

Procedure

This compound was prepared from 5-benzyloxy-2-nitrobenzamide (2.7 g, 56 mmol) in the manner described for 4-amino-3-fluorophenol, affording 1.5 g (99%) of 2-amino-5-hydroxybenzamide. 1H-NMR (CDCl3) δ 7.41 (d, J=8.1 Hz, 1H), 7.16 (dd, J=8.1, 1.6 Hz, 1H), 7.13 (d, J=1, 6 Hz, 1H), 3.93 (s, 3H); MS GC-MS (M+=211, RT=6.15 min).

Sources & evidence

ORD record
ord-3a4db595b6b44ba48e835d1bb4708fa2
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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