Sodium borohydride → HCID 10088511, compound

HRID 235272Notes

Reaction equation

HRID 235272 reaction equation
[C:1]([C:4]1[S:24][C:7]2[CH2:8][CH2:9][C:10]3[C:15]([C:6]=2[CH:5]=1)=[N:14][N:13]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)[C:12](=[O:23])[CH:11]=3)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([C:4]1[S:24][C:7]2[CH2:8][CH2:9][C:10]3[C:15]([C:6]=2[CH:5]=1)=[N:14][N:13]([C:16]1[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=1)[C:12](=[O:23])[CH:11]=3)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10640617HCID 10640617, compound

Product 1

HCID 10088511HCID 10088511, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 600 mg of 8-acetyl-5,6-dihydro-2-(4-methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one in 100 ml of methanol was added 70 mg of sodium borohydride with stirring under ice-cooling. The mixture was stirred for 3 hours and poured into ice-cold water and then extracted with chloroform. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a silica gel (SiO2 :20 g) column using a mixed solvent of chloroform and methanol (98:2) as an eluent. The resulting solid was recrystallized from a mixed solvent of ethyl acetate and hexane to give 300 mg of 8-(1-hydroxyethyl)-5,6-dihydro-2-(4-methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one as a pale yellow powder, melting at 146°-148° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 3 hours
  3. additionpoured into ice-cold water
  4. extractionextracted with chloroform
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on a silica gel (SiO2 :20 g) column
  9. customThe resulting solid was recrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-50a73dce7cdb4c93a8bd5001140df0f8
Source dataset
uspto-grants-1997_01
Patent number
US05597918

Reaction notes

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