Water → HCID 10695552, compound

HRID 622731Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]([CH3:24])=[C:5]([C:20]([O:22][CH3:23])=[O:21])[CH:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:7]=1[C:8]([OH:10])=[O:9].[Br:25][CH2:26][CH2:27][CH2:28][CH2:29]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:24][C:4]1[NH:3][C:2]([CH3:1])=[C:7]([C:8]([O:10][CH2:29][CH2:28][CH2:27][CH2:26][Br:25])=[O:9])[CH:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:5]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension comprising 9.96 g of 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-5-methoxycarbonyl-pyridine-3-carboxylic acid, 5.4 ml of 1,4-dibromobutane and 2.07 g of potassium carbonate in 60 ml of dimethylformamide was heated at 50° C. under stirring for 2.5 hours. The mixture was then cooled to room temperature, poured into 400 ml of water and extracted with diethyl ether. The ethereal extracts were then dried on anhydrous sodium sulfate and evaporated to dryness to give an oil which was purified by flash chromatography on silica gel columns, employing first chloroform and then chloroform:ethyl acetate 97:3 by volume as eluent.

Workup

temperatureThe mixture was then cooled to room temperature
extractionextracted with diethyl ether
dry with materialThe ethereal extracts were then dried on anhydrous sodium sulfate
customevaporated to dryness
customto give an oil which
customwas purified by flash chromatography on silica gel columns

Sources & evidence

ORD record: ord-3b941b76203c485e8171d1eb5297d44b
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04772621

Reaction notes

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