Dimethylformamide → 4-(3-dimethylaminopropyl)-5-formyl-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 1372401Notes

Reaction equation

HRID 1372401 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])=[CH:9][NH:8][C:7]=1[CH3:17])=[O:5])[CH3:2].P(Cl)(Cl)(Cl)=O.CN(C)[CH:25]=[O:26]>>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])=[C:9]([CH:25]=[O:26])[NH:8][C:7]=1[CH3:17])=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 54559518HCID 54559518, compound

Product 1

HCID 542399104-(3-dimethylaminopropyl)-5-formyl-2-methyl-1H-pyrrole-3-carboxylic acid ethyl esterYield 96%

Procedure

4-(3-Dimethylamino-propyl)-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (600 mg, 2.5 mmol) was formylated using phosphorus oxychloride and dimethylformamide to give 645 mg (96% yield) of 4-(3-dimethylamino-propyl)-5-formyl-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 12.15 (br s, 1H, NH), 9.59 (s, 1H, CHO), 4.19 (q, 2H, OCH2), 2.93 (m, 2H, CH2), 2.41 (s, 3H, CH3), 2.18 (m, 2H, CH2), 2.09 (s, 6H, N(CH3)2), 1.63 (m, 2H, CH2), 1.27 (t, 3H, CH3). MS m/z 266 [M+].

Sources & evidence

ORD record
ord-6853e552089b4f138445dfdcb903ec56
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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