Sodium borohydride → 1-hexyl-3-hydroxymethyl-4-methoxy-6-methyl-2(1H)-quinolinone

HRID 36049Notes

Reaction equation

HRID 36049 reaction equation
[CH2:1]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[C:10]([O:18][CH3:19])=[C:9]([CH:20]=[O:21])[C:8]1=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[BH4-].[Na+]>CO.O>[CH2:1]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[C:10]([O:18][CH3:19])=[C:9]([CH2:20][OH:21])[C:8]1=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 152333661-hexyl-3-formyl-4-methoxy-6-methyl-2(1H)-quinolinone

Product 1

HCID 97964601-hexyl-3-hydroxymethyl-4-methoxy-6-methyl-2(1H)-quinolinone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-hexyl-3-formyl-4-methoxy-6-methyl-2(1H)-quinolinone (Step (2) of Example 1, 10 g) in methanol (80 ml) was cooled in an ice-bath and stirred while adding, in small lots, solid sodium borohydride (0.5 g). After stirring for an additional 5 mins the reaction mixture was carefully diluted with water and extracted with methylene chloride. The extracts are dried and evaporated under reduced pressure. The crude product is chromatographed on silica-gel. Elution with 30% acetone-hexane gave 1-hexyl-3-hydroxymethyl-4-methoxy-6-methyl-2(1H)-quinolinone. That the expected product was obtained was confirmed by the spectral data: MS: m/e 303 (M+); NMR (CDCl3): δ4.0 (s, H, OCH3), 4.75 (d, 2H, CH2O).

Workup

  1. stirringAfter stirring for an additional 5 mins the reaction mixture
  2. extractionextracted with methylene chloride
  3. customThe extracts are dried
  4. customevaporated under reduced pressure
  5. customThe crude product is chromatographed on silica-gel
  6. washElution with 30% acetone-hexane

Sources & evidence

ORD record
ord-1c45a33dcb0e47fd8d3d4a2267f9c22e
Source dataset
uspto-grants-1995_05
Patent number
US05412104

Reaction notes

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