Acetic Anhydride → HCID 56609064, compound

HRID 477183Notes

Reaction equation

HRID 477183 reaction equation
[C:1]1([C:7](=[N:28][OH:29])[CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]4)=[O:16])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:30](OC(=O)C)(=[O:32])[CH3:31].C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.O>[C:1]1([C:7](=[N:28][O:29][C:30](=[O:32])[CH3:31])[CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]4)=[O:16])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 73474322HCID 73474322, compound

Product 1

HCID 56609064HCID 56609064, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5.3 Grams of 6-[4-(2-phenyl-2-hydroxyiminoethyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril, 1.91 ml of acetic anhydride and 5.64 ml of triethylamine were dissolved in 60 ml of methylene chloride, and the resulting solution was stirred overnight at room temperature. After the reaction was completed, the reaction mixture was poured into water, and was made alkaline by adding sodium carbonate, then this mixture was extracted with methylene chloride. The methylene chloride extract was dried, then the solvent was removed by evaporation, and the residue was converted into an oxalate by stirring with oxalic acid in acetone. The oxalate was recrystallized from ethanol-water to yield 5.28 g of 6-[4-(2-phenyl-2-acetoxyiminoethyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril.oxalate.monohydrate.

Workup

  1. extractionthis mixture was extracted with methylene chloride
  2. extractionThe methylene chloride extract
  3. customwas dried
  4. customthe solvent was removed by evaporation
  5. stirringby stirring with oxalic acid in acetone
  6. customThe oxalate was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-2d9dbc8d535540ffbdda65b1b8a4e30c
Source dataset
uspto-grants-1989_12
Patent number
US04886809

Reaction notes

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