Water → HCID 10695552, compound

HRID 247094Notes

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-3ca39dc4917b45daa5b2fe72ae6685c3
Source dataset: uspto-grants-1987_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04705797

Reaction notes

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