Potassium Acetate → HCID 23353990, compound

HRID 235273Notes

Reaction equation

HRID 235273 reaction equation
Cl[CH2:2][C:3]([C:5]1[S:25][C:8]2[CH2:9][CH2:10][CH:11]3[C:16]([C:7]=2[CH:6]=1)=[N:15][N:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)[C:13](=[O:24])[CH2:12]3)=[O:4].[C:26]([O-:29])(=[O:28])[CH3:27].[K+]>C(O)(=O)C>[C:26]([O:29][CH2:2][C:3]([C:5]1[S:25][C:8]2[CH2:9][CH2:10][CH:11]3[C:16]([C:7]=2[CH:6]=1)=[N:15][N:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)[C:13](=[O:24])[CH2:12]3)=[O:4])(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 23353985HCID 23353985, compound

Product 1

HCID 23353990HCID 23353990, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 5.8 g of 8-chloroacetyl-4,4a,5,6-tetrahydro-2-(4-methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one in 100 ml of acetic acid was added 12 g of potassium acetate and the mixture was stirred for 5 hours. The mixture was poured into ice-cold water and the precipitate was collected by filtration. The filtrate was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue and the precipitate were combined and chromatographed on a silica gel (SiO2 :200 g) column using chloroform as an eluent. The resulting crystals were recrystallized from a mixed solvent of chloroform and methanol to give 4.4 g of 8-acetoxyacetyl-4,4a, 5,6-tetrahydro-2-(4-methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one as a white powder, melting at 144°-145° C.

Workup

  1. additionThe mixture was poured into ice-cold water
  2. filtrationthe precipitate was collected by filtration
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customchromatographed on a silica gel (SiO2 :200 g) column
  8. customThe resulting crystals were recrystallized from a mixed solvent of chloroform and methanol

Sources & evidence

ORD record
ord-6fbd958e449040d290ef65678a1c2f20
Source dataset
uspto-grants-1997_01
Patent number
US05597918

Reaction notes

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