Acetic Anhydride → HCID 14988347, compound

HRID 1087153Notes

Reaction equation

HRID 1087153 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:34])=[C:5]([C:21]([O:23][CH2:24]/[CH:25]=[CH:26]/[C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[C:35](OC(=O)C)(=[O:37])[CH3:36]>N1C=CC=CC=1>[CH3:1][C:2]1[NH:3][C:4]([CH3:34])=[C:5]([C:21]([O:23][CH2:24]/[CH:25]=[CH:26]/[C:27]2[CH:28]=[CH:29][C:30]([O:33][C:35](=[O:37])[CH3:36])=[CH:31][CH:32]=2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13533254HCID 13533254, compound

Product 1

HCID 14988347HCID 14988347, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.5 Gram of methyl 3-(4-hydroxyphenyl)-2(E)-propenyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate was dissolved in 5 ml of pyridine, then to this solution was added 0.5 ml of acetic anhydride under an ice-cooling condition. The reaction mixture was allowed to stand overnight, then poured into an ice-water, and extracted with ether. The ether layer was washed with a diluted hydrochloric acid, 10%-sodium bicarbonate aqueous solution and water in this order, then dried with anhydrous sodium sulfate. The ether extract was concentrate, and the residue thus obtained was purified by means of a silica gel column chromatography (eluent: methanol:chloroform=1:100) to yield 0.4 g of methyl 3(4-acetyloxyphenyl)-2(E)-propenyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate in the form of light yellow indefinite form crystals.

Workup

  1. temperaturecooling condition
  2. extractionextracted with ether
  3. washThe ether layer was washed with a diluted hydrochloric acid, 10%-sodium bicarbonate aqueous solution and water in this order
  4. dry with materialdried with anhydrous sodium sulfate
  5. extractionThe ether extract
  6. concentrationwas concentrate
  7. customthe residue thus obtained
  8. customwas purified by means of a silica gel column chromatography (eluent: methanol:chloroform=1:100)

Sources & evidence

ORD record
ord-ff09ea343e2e4e569216e53e71493c4c
Source dataset
uspto-grants-1991_07
Patent number
US05034395

Reaction notes

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