Methanol → HCID 67775610, compound

HRID 533408Notes

Reaction equation

HRID 533408 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][CH:13]=2)[C:8]([C:19]2[C:24]([F:25])=[CH:23][C:22]([F:26])=[CH:21][C:20]=2[F:27])=[N:7][CH:6]=1)=[O:4].CO>O>[OH:4][CH2:3][C:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][CH:13]=2)[C:8]([C:19]2[C:20]([F:27])=[CH:21][C:22]([F:26])=[CH:23][C:24]=2[F:25])=[N:7][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86666253HCID 86666253, compound

Product 1

HCID 67775610HCID 67775610, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium borohydride (17 mg) was added to a mixture of methyl 4-formyl-1-(2,4,6-trifluorophenyl)isoquinoline-7-carboxylate (150 mg) and methanol (10 mL) under ice-cooling, followed by stirring at room temperature for 10 minutes. The reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with water, dried, and then concentrated under reduced pressure to obtain methyl 4-(hydroxymethyl)-1-(2,4,6-trifluorophenyl)isoquinoline-7-carboxylate (140 mg).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7c9fe6c4204645ffa4388ce9e3c632f8
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

Loading…