Water → HCID 23019632, compound

HRID 1354190Notes

Reaction equation

HRID 1354190 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][N:11]3[C:16]([C:17]=2[CH3:18])=[C:15]([CH:19]2[CH2:21][CH2:20]2)[CH:14]=[C:13]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:12]3=[O:27])=[CH:4][CH:3]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29].O>N1C=CC=CC=1>[C:28]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][N:11]3[C:16]([C:17]=2[CH3:18])=[C:15]([CH:19]2[CH2:21][CH2:20]2)[CH:14]=[C:13]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:12]3=[O:27])=[CH:6][CH:7]=1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 23019679HCID 23019679, compound

Product 1

HCID 23019632HCID 23019632, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

50 mg of ethyl 8-(4-aminophenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (Example 2) was dissolved in 2 ml of pyridine. 17 mg of acetic anhydride was added to the obtained solution, and they were stirred at room temperature for 16 hours. Water was added to the reaction mixture. After the extraction with chloroform, the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduce pressure, and the obtained residue was purified by the silica gel column chromatography (eluent: chloroform/ethyl acetate=4/1) to obtain 55 mg of ethyl 8-(4-acetylaminophenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate.

Workup

  1. extractionAfter the extraction with chloroform
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customThe solvent was evaporated
  4. customthe obtained residue was purified by the silica gel column chromatography (eluent: chloroform/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-ceebd21d956f45408560c8944599256f
Source dataset
uspto-grants-2007_05
Patent number
US07223773B2

Reaction notes

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