Sodium borohydride → (3-Chloroisoquinolin-4-yl)methanol

HRID 1471699Notes

Reaction equation

HRID 1471699 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]=1[CH:12]=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]=1[CH2:12][OH:13])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 145672793-Chloroisoquinoline-4-carbaldehyde

Product 1

HCID 86690749(3-Chloroisoquinolin-4-yl)methanolYield 41.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To 3-chloroisoquinoline-4-carbaldehyde (220 mg, crude) in THF (10 mL) was added NaBH4 (155 mg, 4.08 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 h, acidified to pH 3, and extracted with EtOAc. The combined organic layers were washed with saturated sodium bicarbonate solution and brine, dried over Na2SO4, filtered, and concentrated to give a crude solid. The crude was purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-chloroisoquinolin-4-yl)methanol (92 mg, 24% for three steps). LRMS (M+H+) m/z 194.0.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with saturated sodium bicarbonate solution and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude solid
  7. customThe crude was purified on silica gel using
  8. additiona mixture of EtOAc and hexanes as eluent

Sources & evidence

ORD record
ord-a3441693e3294eb1915e45af405a3315
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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