Formaldehyde → HCID 54698218, compound

HRID 2214569Notes

Reaction equation

HRID 2214569 reaction equation
CO[C:3](=[O:21])[C:4]([OH:20])=[CH:5][C:6](=[O:19])[N:7]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=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>>[F:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][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:17][CH:16]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 6329MethylamineHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 72646461HCID 72646461, compound

Product 1

HCID 54698218HCID 54698218, compoundYield 38%

Procedure

3-{[2-(4-Fluorophenyl)-ethyl]-methoxy-carbamoyl}-2-hydroxy-acrylic acid methyl ester (Compound 52-D) was treated with paraformaldehyde and methylamine as described in the preparation of Compound 12 to give the title compound as a white solid (38% yield); mp 157° C. dec. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.96 (2H, t, J=7.6 Hz, CH2), 3.14 (3H, s, NCH3), 3.71 (3H, s, OCH3), 3.93 (2H, t, J=7.6 Hz, CH2), 4.14 (2H, s, NCH2), 7.01 (2H, m, aromatics), 7.2 (2H, m, aromatics), 11.55 (1H, broad s, OH). Anal. calcd for C15H17FN2O4: C, 58.44; H, 5.56; N, 9.09. Found: C, 58.52; H, 5.66; N, 8.89.

Sources & evidence

ORD record
ord-db4cdf189431437293a7f86ee925d12b
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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