2-Methoxy-4-nitrophenol → 4-Aminoguaiacol

HRID 658450Notes

Reaction equation

HRID 658450 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([O:11][CH3:12])[CH:5]=1)([O-])=O.NC1C=CC(O)=CC=1F>>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([O:11][CH3:12])[CH:5]=1

Participants

3

Reactant 2

HCID 767382-Methoxy-4-nitrophenolHCID 27359194-Amino-3-fluorophenol

Product 1

HCID 1012964-AminoguaiacolYield 63.2%

Procedure

This compound was prepared from 4-nitro-2-methoxyphenol (10.0 g, 59.1 mmol) in the manner described for 4-amino-3-fluorophenol, affording 5.20 g (56.9%) of 4-amino-2-methoxyphenol as a dark brown solid. 1H-NMR (DMSO-d6) δ 7.79 (br s, 1H), 6.44 (d, J=8.1 Hz, 1H), 6.21 (d, J=2.4 Hz, 1H), 5.97 (dd, J=8.4, 2.4 Hz, 1H), 4.43 (br s, 2H), 3.65 (s, 3H); TLC (66% EtOAc/Hex), Rf=0.42.

Sources & evidence

ORD record
ord-2a694ca794ab46cc94b3ea63a90988fa
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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