Methanol → 4-Hydroxy-1-methyl-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid [3-(3,4-dichlorophenyl)-propyl]-methyl-amide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][N:12]([CH3:24])[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.[CH3:27][NH2:28].[CH3:29]O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][N:12]([CH3:24])[C:13]([C:14]2[CH2:27][N:28]([CH3:29])[C:19](=[O:20])[C:15]=2[OH:16])=[O:23])[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
Reactant 3
Product 1
Procedure
Reaction of N-[3-(3,4-dichlorophenyl)-propyl]-2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-methyl-acetamide (0.570 g, 1.53 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 0.287 g (52% yield) of the title compound as white crystals; mp 138–140° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm); 1.80 (2H, m, CH2), 2.49 (2H, t, J=7.6 Hz, CH2), 2.92 (3H, s, NCH3), 2.95 (3H, s, NCH3), 3.31 (2H, broad t, J=7.3 Hz, NCH2), 3.87 (2H, broad s, NCH2), 6.91 (1H, dd, J=2.0 Hz and J=8.1 Hz, aromatic), 7.16 (1H, d, J=2.0 Hz, aromatic), 7.23 (1H, d, J=8.1 Hz, aromatic), 10.94 (1H, broad s, OH). Anal. Calcd for C6H18Cl2N2O3: C, 53.80; H, 5.08; N, 7.84. Found: C, 53.90; H, 5.17; N, 7.83.
Sources & evidence
- ORD record
- ord-14e04ef1443148f288c28184c4331ae5
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109186B2
Reaction notes
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