1-(6-chloro-2-methyl-4-phenylquinolin-3-yl)ethanone → HCID 46214905, compound

HRID 1184032Notes

Reaction equation

HRID 1184032 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([C:13](=[O:15])[CH3:14])=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([CH:13]([OH:15])[CH3:14])=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6722621-(6-chloro-2-methyl-4-phenylquinolin-3-yl)ethanoneHCID 4311764Sodium borohydride

Product 1

HCID 46214905HCID 46214905, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(6-chloro-2-methyl-4-phenylquinolin-3-yl)ethanone (550 mg, 1.8 mmol) in methanol (10 ml) at room temperature was added portionwise sodium borohydride (315 mg, 8.3 mmol). After the addition the reaction was stirred for 3 hours. Most of the solvent was removed under reduced pressure, the residue diluted with ethyl acetate, and the mixture was poured into a separatory funnel. The organic layer was washed with water (2×), saturated sodium bicarbonate, then brine. The organic phase was separated and solvent removred under reduced pressure to provide 1-(6-chloro-2-methyl-4-phenylquinolin-3-yl)ethanol (460 mg, 83%) as a white powder. TLC Rf=0.4 using 1:1 ethyl acetate:hexanes as eluent. 1H NMR (CDCl3, 400 MHz) δ 7.88 (d, 1H, J=8.9 Hz); 7.54-7.42 (m, 4H); 7.18-7.08 (m, 3H); 5.05 (q, 1H, J=7.0 Hz); 2.95 (s, 3H); 1.0 (d, 3H, J=6.65 Hz). LCMS (CI) shows M+H 297.

Workup

  1. additionAfter the addition the reaction
  2. customMost of the solvent was removed under reduced pressure
  3. additionthe residue diluted with ethyl acetate
  4. additionthe mixture was poured into a separatory funnel
  5. washThe organic layer was washed with water (2×), saturated sodium bicarbonate
  6. customThe organic phase was separated

Sources & evidence

ORD record
ord-33414e5d9b1b4d23827f837a674bd6ab
Source dataset
uspto-grants-2014_03
Patent number
US08664399B2

Reaction notes

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