Water → HCID 23353995, compound

HRID 235275Notes

Reaction equation

HRID 235275 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[S:27][C:10]2[CH2:11][CH2:12][CH:13]3[C:18]([C:9]=2[CH:8]=1)=[N:17][N:16]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)[C:15](=[O:26])[CH2:14]3)(=O)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[OH:4][CH2:5][CH2:6][C:7]1[S:27][C:10]2[CH2:11][CH2:12][CH:13]3[C:18]([C:9]=2[CH:8]=1)=[N:17][N:16]([C:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=1)[C:15](=[O:26])[CH2:14]3

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 23353989HCID 23353989, compound

Product 1

HCID 23353995HCID 23353995, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1.5 g of 8-(2-acetoxyethyl) -4,4a, 5,6-tetrahydro-2-(4-methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one in 50 ml of methanol was added 5 ml of aqueous solution of 0.7 g of potassium carbonate under ice-cooling. The mixture was stirred for an hour, and poured into water and then extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting solid was recrystallized from a mixed solvent of chloroform and ethanol to give 1.3 g of 4,4a,5,6-tetrahydro-8-(2-hydroxy-ethyl)-2-(4-methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one as a white powder, melting at 159°-160° C.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid was recrystallized from a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-606e2c80c854402387b50edbee93380e
Source dataset
uspto-grants-1997_01
Patent number
US05597918

Reaction notes

Loading…