Methanol → 4-Hydroxy-1-methyl-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid [3-(3,4-dichlorophenyl)-propyl]-amide

HRID 2214721Notes

Reaction equation

HRID 2214721 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:23])[CH:14]=[C:15]2[C:19](=[O:20])OC(C)(C)[O:16]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C=O.[CH3:26][NH2:27].[CH3:28]O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH:12][C:13]([C:14]2[CH2:26][N:27]([CH3:28])[C:19](=[O:20])[C:15]=2[OH:16])=[O:23])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 22018472Paraformaldehyde methylamineHCID 69655965n-[3-(3,4-Dichlorophenyl)-propyl]-2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-acetamide

Product 1

HCID 547046224-Hydroxy-1-methyl-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid [3-(3,4-dichlorophenyl)-propyl]-amideYield 56%

Procedure

Reaction of N-[3-(3,4-dichlorophenyl)-propyl]-2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-acetamide (0.432 g, 1.20 mmol) with the paraformaldehyde-methylamine adduct in methanol using a procedure similar to the one described in the preparation of compound 44 (method 44B) gave 0.232 g (56% yield) of the title compound as white crystals; mp 157–158° C. (dec) (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm); 1.81 (2H, m, CH2), 2.57 (2H, t, J=7.5 Hz, CH2), 3.05 (3H, s, NCH3), 3.33 (2H, m, NCH2), 3.98 (2H, s, NCH2), 6.95 (1H, broad t, NH), 7.05 (1H, broad dd, aromatic), 7.21 (1H, d, J=2 Hz, aromatic), 7.26 (1H, d, J=8.1 Hz, aromatic), 10.13 (1H, broad, OH). Anal. Calcd for C5H16Cl2N2O3: C, 52.49; H, 4.70; N, 8.16. Found: C, 52.39; H, 4.80; N, 7.89.

Sources & evidence

ORD record
ord-6735bd7b4e724b95ba951cdee7e4a1b1
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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