Formaldehyde → 4-hydroxy-N-methoxy-1-methyl-5-oxo-N-(p-tolylmethyl)-2H-pyrrole-3-carboxamide

HRID 2214598Notes

Reaction equation

CO[C:3](=[O:20])[C:4]([OH:19])=[CH:5][C:6](=[O:18])[N:7]([O:16][CH3:17])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1.C=O.CN.ClC1C=C(C=CC=1Cl)[CH2:29][N:30](C)[C:31](C1CN(C)C(=O)C=1O)=O>>[CH3:17][O:16][N:7]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=1)[C:6]([C:5]1[CH2:29][N:30]([CH3:31])[C:3](=[O:20])[C:4]=1[OH:19])=[O: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 723950842-Hydroxy-3-[methoxy-(4-methylbenzyl)-carbamoyl]-acrylic acid methyl ester2×

Product 1

HCID 546982254-hydroxy-N-methoxy-1-methyl-5-oxo-N-(p-tolylmethyl)-2H-pyrrole-3-carboxamideYield 41%

Procedure

2-Hydroxy-3-[methoxy-(4-methylbenzyl)-carbamoyl]-acrylic acid methyl ester (Compound 59-A) was treated with paraformaldehyde and methylamine as described in the preparation of Compound 12 to give the title compound as a white solid (41% yield); mp 150–152° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.4 (3H, s, CH3), 3.16 (3H, s, NCH3), 3.78 (3H, s, OCH3), 4.21 (2H, s, NCH2), 4.91 (2H, s, NCH2), 7.22 (2H, d, J=8 Hz, aromatics), 7.28 (2H, d, J=8 Hz, aromatics), 11.7 (1H, broad s, OH). Anal. calcd for C15H18N2O4: C, 62.05; H, 6.24; N, 9.65. Found: C, 61.91; H, 6.30; N, 9.56.

Sources & evidence

ORD record: ord-9b0e8b2531af4c009edb6224d7992db5
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109186B2

Reaction notes

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