(5-Amino-2-methoxyphenyl)methanol → 3-Hydroxymethyl-4-propyloxyaniline

HRID 500429Notes

Reaction equation

HRID 500429 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:12][CH2:13][CH2:14][CH3:15])=[C:8]([CH:11]=1)[CH2:9][OH:10])([O-])=O.OCC1C=C(C=CC=1OC)N>>[OH:10][CH2:9][C:8]1[CH:11]=[C:4]([CH:5]=[CH:6][C:7]=1[O:12][CH2:13][CH2:14][CH3:15])[NH2:1]

Participants

3

Reactant 2

HCID 237567(5-Amino-2-methoxyphenyl)methanolHCID 21904358(5-Nitro-2-propoxyphenyl)methanol

Product 1

HCID 219043683-Hydroxymethyl-4-propyloxyanilineYield 37%

Procedure

This compound was prepared by reduction of 5-nitro-2-propyloxy-benzylalcohol using the method described for the preparation of 3-hydroxymethyl-4-methoxyaniline in 37% yield: 1H NMR (DMSO-d6, 500 MHz) δ 6.66 (d, 1H, J=2.5 Hz), 6.60 (d, 1H, J=8.6 Hz), 6.35 (dd, 1H, J=2.7 and 8.5 Hz), 4.79 (t, 1H, J=5.8 Hz), 4.54 (br, 2H), 4.37 (d, 2H, J=6.1 Hz), 3.74 (t, 2H, J=6.4 Hz), 1.65 (m, 2H), 0.94 (t, 3H, J=7.4 Hz).

Sources & evidence

ORD record
ord-c1defbcc5f7b4734b95d67f6cf376059
Source dataset
uspto-grants-2010_08
Patent number
US07772216B2

Reaction notes

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