Sodium borohydride → HCID 67199050, compound

HRID 1948720Notes

Reaction equation

HRID 1948720 reaction equation
[BH4-].[Na+].[C:3]1([C:9]2[C:18]([CH:19]=[O:20])=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[C:3]1([C:9]2[C:18]([CH2:19][OH:20])=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 121916842-phenyl-quinoline-3-carbaldehyde

Product 1

HCID 67199050HCID 67199050, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (45 mg, 1.18 mmol) was added to a solution of 2-phenyl-quinoline-3-carbaldehyde (212 mg, 0.91 mmol) in MeOH (7 mL) and the reaction mixture was stirred at r.t. for 1 h. The reaction was quenched by the addition of glacial AcOH (0.1 mL) and the solvent was removed in vacuo. The residue was partitioned between EtOAc and 10% aqueous K2CO3 solution. The organic phase was dried (MgSO4) and the solvent removed in vacuo to give the title compound (quantitative) as a clear oil which crystallized on standing to a yellow solid. δH (CDCl3) 8.32 (s, 1H), 8.12-8.19 (m, 1H), 7.80-7.86 (m, 1H), 7.67-7.74 (m, 1H), 7.50-7.59 (m, 3H), 7.37-7.47 (m, 3H), 4.71 (s, 2H), 2.76 (br. s, 1H). LCMS (ES+) 236.1 (M+H)+, RT 3.04 minutes (Method 4).

Workup

  1. customThe reaction was quenched by the addition of glacial AcOH (0.1 mL)
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between EtOAc and 10% aqueous K2CO3 solution
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-dd09671b5e344f83af3586a3e3b8e5a1
Source dataset
uspto-grants-2013_03
Patent number
US08399483B2

Reaction notes

Loading…