m-Formylbenzonitrile → [3-(Aminomethyl)phenyl]methanol

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7])#[N:2].C(OC1C=C(C=C(OCC2C=CC=CC=2)C=1)CN)C1C=CC=CC=1>>[OH:7][CH2:6][C:5]1[CH:4]=[C:3]([CH:10]=[CH:9][CH:8]=1)[CH2:1][NH2:2]

Participants

Reactant 2

HCID 90670m-Formylbenzonitrile

HCID 15505554[3,5-Bis(benzyloxy)benzyl]amine hydrochloride

Product 1

HCID 21880609[3-(Aminomethyl)phenyl]methanolYield 66%

Procedure

This compound was prepared by reduction of 3-cyanobenzaldehyde according to the procedure described in preparation of 3,5-dibenzyloxybenzylamine. Yield was 66%: 1H NMR (Acetone-d6, 500 MHz) δ 7.32 (s, 1H), 7.23 (dd, 1H, J=7.6 and 7.0), 7.19, complex, 2H), 4.59 (s, 2H), 4.40 (s, 2H), 4.10 (br, 1H), 1.96 (br, 1H), 1.88 (br, 1H).

Sources & evidence

ORD record: ord-b76b6ae21fe944ad8b04497ca70cb28e
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427608B2

Reaction notes

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