Hydrochloric Acid → HCID 23353984, compound

HRID 235264Notes

Reaction equation

HRID 235264 reaction equation
[CH:1]([C:3]1[S:24][C:6]2[CH2:7][CH2:8][CH2:9][C:10]3[C:11](=[N:12][N:13]([C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=4)[C:14](=[O:16])[CH:15]=3)[C:5]=2[CH:4]=1)=[O:2].[BH4-].[Na+].Cl>CO>[OH:2][CH2:1][C:3]1[S:24][C:6]2[CH2:7][CH2:8][CH2:9][C:10]3[C:11](=[N:12][N:13]([C:17]4[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=4)[C:14](=[O:16])[CH:15]=3)[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 23354006HCID 23354006, compound

Product 1

HCID 23353984HCID 23353984, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1.4 g of 9-formyl-2-(4-methylphenyl)-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one in methanol was added 1.0 g of sodium borohydride under ice-cooling. After stirring for an hour, the mixture was poured into diluted hydrochloric acid and 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 column using chloroform as an eluent. The solid was recrystallized from a mixed solvent of ethanol and isopropyl ether to give 1.0 g of 9-hydroxymethyl-2-(4-methylphenyl)-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one as a white powder, melting at 158°-159° C.

Workup

  1. temperaturecooling
  2. extractionextracted with chloroform
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on a silica gel column
  7. customThe solid was recrystallized from a mixed solvent of ethanol and isopropyl ether

Sources & evidence

ORD record
ord-73584c2e2d4a4c8da13ec1c15e6b7d61
Source dataset
uspto-grants-1997_01
Patent number
US05597918

Reaction notes

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