3-{[(2-Hydroxy-ethyl)-methyl-amino]-methyl}-benzonitrile → HCID 178484507, compound

HRID 219906Notes

Reaction equation

HRID 219906 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][N:20]([CH2:22]C1C=C(C=CC=1)C#N)[CH3:21]>>[OH:16][NH:15][C:2](=[NH:1])[C:3]1[CH:4]=[CH:5][CH:6]=[C:11]([CH2:21][N:20]([CH2:19][CH2:18][OH:17])[CH3:22])[CH:12]=1

Participants

3

Reactant 2

HCID 391615223-{[(2-Hydroxy-ethyl)-methyl-amino]-methyl}-benzonitrileHCID 72307497Methyl 4-[amino(hydroxyimino)methyl]-3-methoxybenzoate

Product 1

HCID 178484507HCID 178484507, compoundYield 99%

Procedure

The title compound was obtained following procedure and work up described for Intermediate 47 step 2 but starting from 3-{[(2-Hydroxy-ethyl)-methyl-amino]-methyl}-benzonitrile obtained in step 1 (4.9 g, 26.28 mmol) to give the title compound as white gummy solid (5.7 g, 99%). 1H NMR (DMSO-d6, 400 MHz) δ 9.58 (s, 1H), 7.60 (s, 1H), 7.51-7.54 (m, 1H), 7.28-7.31 (m, 2H), 5.76-7.83 (s, 2H), 4.38 (bs, 1H), 3.48-3.51 (m, 4H), 2.40-2.43 (m, 2H), 2.13 (m, 3H). LC/MS (Method A): 224.1 (M+H)+. HPLC (Method B): Rt 0.7 min, (Purity 91.1%).

Sources & evidence

ORD record
ord-0df3510b64fa4e698d899135c43a8cce
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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