3-[(2-Hydroxyethoxy)methyl]benzonitrile → N'-hydroxy-3-[(2-hydroxyethoxy)methyl]benzenecarboximidamide

HRID 219903Notes

Reaction equation

HRID 219903 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][O:20][CH2:21]C1C=C(C=CC=1)C#N>>[OH:16][N:15]=[C:2]([C:3]1[CH:4]=[CH:5][CH:6]=[C:11]([CH2:21][O:20][CH2:19][CH2:18][OH:17])[CH:12]=1)[NH2:1]

Participants

3

Reactant 2

HCID 284140323-[(2-Hydroxyethoxy)methyl]benzonitrileHCID 72307497Methyl 4-[amino(hydroxyimino)methyl]-3-methoxybenzoate

Product 1

HCID 74559374N'-hydroxy-3-[(2-hydroxyethoxy)methyl]benzenecarboximidamide

Procedure

The title compound was obtained following procedure and work up described for Intermediate 47 step 2 but starting from 3-[(2-hydroxyethoxy)methyl]benzonitrile obtained in step 1 (0.90 g; 5.08 mmol) to give the title compound as a yellowish oil (1.26 g, quantitative). 1H NMR (DMSO-d6, 300 MHz) δ 9.61 (s, 1H), 7.64 (bs, 1H), 7.60-7.55 (m, 1H), 7.37-7.31 (m, 2H), 5.75 (bs, 2H), 4.66-4.62 (m, 1H), 4.50 (s, 2H), 3.56-3.51 (m, 2H), 3.48-3.44 (m, 2H). LC/MS (Method B): 211.1 (M+H)+.

Sources & evidence

ORD record
ord-75780524df324e3d8a82f7ec2e21d24d
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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