Formaldehyde → N-[(4-cyanophenyl)methyl]-4-hydroxy-N-methoxy-1-methyl-5-oxo-2H-pyrrole-3-carboxamide

HRID 2214612Notes

Reaction equation

CO[C:3](=[O:21])[C:4]([OH:20])=[CH:5][C:6](=[O:19])[N:7]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)[O:8][CH3:9].C=O.CN.ClC1C=C(C=CC=1Cl)[CH2:30][N:31](C)[C:32](C1CN(C)C(=O)C=1O)=O>>[C:17]([C:14]1[CH:13]=[CH:12][C:11]([CH2:10][N:7]([O:8][CH3:9])[C:6]([C:5]2[CH2:30][N:31]([CH3:32])[C:3](=[O:21])[C:4]=2[OH:20])=[O:19])=[CH:16][CH:15]=1)#[N:18]

Participants

Reactant 4

HCID 712Formaldehyde

HCID 6329Methylamine

HCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamide

HCID 86760253HCID 86760253, compound

Product 1

HCID 54698228N-[(4-cyanophenyl)methyl]-4-hydroxy-N-methoxy-1-methyl-5-oxo-2H-pyrrole-3-carboxamideYield 46%

Procedure

3-[(4-Cyanobenzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 62-D) was treated with paraformaldehyde and methylamine as described in the preparation of Compound 12 to give the title compound as a white solid (46% yield); mp 161° C. dec. 1HNMR 400 MHz (CDCl3) δ (ppm): 3.11 (3H, s, NCH3), 3.75 (3H, s, OCH3), 4.17 (2H, s, NCH2), 4.93 (2H, s, NCH2), 7.44 (2H, d, J=8.2 Hz, aromatics), 7.65 (2H, d, J=8.2 Hz, aromatics). Anal. calcd for C15H15N3O4: C, 59.79; H, 5.01; N, 13.94. Found: C, 59.51; H, 4.90; N, 13.69.

Sources & evidence

ORD record: ord-8b5ef74db0de4acbbf783c6d97dae862
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109186B2

Reaction notes

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