Water → HCID 23369632, compound

HRID 1900737Notes

Reaction equation

HRID 1900737 reaction equation
[CH:1]([CH:3]1[C:15]2[C:6](=[C:7]3[C:12](=[C:13]([CH3:16])[CH:14]=2)[NH:11][C:10](=[O:17])[CH:9]=[CH:8]3)[O:5][CH2:4]1)=[O:2].[BH4-].[Na+].O>CO>[OH:2][CH2:1][CH:3]1[C:15]2[C:6](=[C:7]3[C:12](=[C:13]([CH3:16])[CH:14]=2)[NH:11][C:10](=[O:17])[CH:9]=[CH:8]3)[O:5][CH2:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 23369777HCID 23369777, compound

Product 1

HCID 23369632HCID 23369632, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 3-formyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (1.0 g) in methanol (80 ml), sodium borohydride (1.0 g) was added and stirred at room temperature for 30 minutes. After completion of the reaction, water was added and extracted with chloroform-methanol (4:1). The extract was dried and the solvent was evaporated. The residue was recrystallized from methanol-ether to obtain 0.59 g of 3-hydroxymethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one was obtained as colorless needles (58.5%).

Workup

  1. additionwas added
  2. extractionextracted with chloroform-methanol (4:1)
  3. customThe extract was dried
  4. customthe solvent was evaporated
  5. customThe residue was recrystallized from methanol-ether

Sources & evidence

ORD record
ord-be5ef88bae404929813abf02d413f729
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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