3-(2-Hydroxyethyl)benzonitrile → N'-hydroxy-3-(2-hydroxyethyl)benzenecarboximidamide

HRID 219900Notes

Reaction equation

HRID 219900 reaction equation
[NH2:1][C:2](=[N:15][OH:16])[C:3]1[CH:12]=[CH:11][C:6](C(OC)=O)=[CH:5][C:4]=1OC.[OH:17][CH2:18][CH2:19]C1C=C(C=CC=1)C#N>>[OH:16][N:15]=[C:2]([C:3]1[CH:4]=[CH:5][CH:6]=[C:11]([CH2:19][CH2:18][OH:17])[CH:12]=1)[NH2:1]

Participants

3

Reactant 2

HCID 149267273-(2-Hydroxyethyl)benzonitrileHCID 72307497Methyl 4-[amino(hydroxyimino)methyl]-3-methoxybenzoate

Product 1

HCID 76662611N'-hydroxy-3-(2-hydroxyethyl)benzenecarboximidamide

Procedure

The title compound was obtained following procedure and work up described for Intermediate 47 step 2 but starting from 3-(2-hydroxy-ethyl)-benzonitrile (2 g, 13.59 mmol). Lyophilization of the reaction mixture gave the title compound as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 9.56 (s, 1H), 7.51-7.46 (m, 2H), 7.28-7.19 (m, 2H), 5.75 (bs, 2H), 4.64 (t, J=5.2 Hz, 1H), 3.63-3.57 (m, 2H), 2.71 (t, J=7.1 Hz, 2H). LC/MS (Method B): 181.1 (M+H)+.

Sources & evidence

ORD record
ord-1be08d2b13a14b4b8a8538eeb80e5991
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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