Sodium borohydride → HCID 68577103, compound

HRID 1949032Notes

Reaction equation

HRID 1949032 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[CH2:5][NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH:17]=[O:18])[CH:13]=2)[N:8]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[CH2:5][NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:17][OH:18])[CH:13]=2)[N:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86629136HCID 86629136, compound

Product 1

HCID 68577103HCID 68577103, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(2-Methoxy-benzylamino)-quinoline-6-carbaldehyde (663 mg, 2.27 mmol) was dissolved in 25 mL methanol and sodium borohydride (343 mg, 9.03 mmol) was added. The reaction mixture was refluxed for 3 h. The solvent was evaporated off. The residue was taken up in 100 mL water and extracted three times with ethyl acetate (100 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The crude product was recrystallized from dichloromethane. [2-(2-Methoxy-benzylamino)-quinolin-6-yl]-methanol was obtained as a white solid (369 mg, 59%), MS: m/e=295.3 (M+H+).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customThe solvent was evaporated off
  3. extractionextracted three times with ethyl acetate (100 mL each)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-181dd53530aa4c948538bbbdd6ba426e
Source dataset
uspto-grants-2013_03
Patent number
US08399674B2

Reaction notes

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