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

Participants

Role	Name	HCID	Charge
Reactant	Formaldehyde	HCID 712	—
Reactant	Methylamine	HCID 6329	—
Reactant	N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamide	HCID 54697551	—
Reactant	2-Hydroxy-3-[methoxy-(4-methylbenzyl)-carbamoyl]-acrylic acid methyl ester	HCID 72395084	—
Product	4-hydroxy-N-methoxy-1-methyl-5-oxo-N-(p-tolylmethyl)-2H-pyrrole-3-carboxamide	HCID 54698225	41%

Reaction Steps

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.

Provenance & Evidence

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