Sodium Hydroxide → (3-Chloroisoquinolin-8-yl)methanol

HRID 920247Notes

Reaction equation

HRID 920247 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:12](O)=[O:13].B.C1COCC1.[OH-].[Na+]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:12][OH:13]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 895248833-Chloroisoquinoline-8-carboxylic acid

Product 1

HCID 89524955(3-Chloroisoquinolin-8-yl)methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-chloroisoquinoline-8-carboxylic acid (0.5 g, 1.803 mmol) in THF (18.03 ml) at 0° C. was treated with BH3.THF (5.41 ml, 5.41 mmol). After stirring for 2 hours at 0° C., 1N NaOH was added. The reaction was stirred for 30 minutes then diluted with EtOAc and the layers were separated. Aqueous layer was washed with EtOAc three times. All combined organic layers were washed with brine, then dried with sodium sulfate. Filtered and concentrated in vacuo. Purified by silica gel chromatography (0-100% EtOAc in hexane) to yield (3-chloroisoquinolin-8-yl)methanol.

Workup

  1. stirringThe reaction was stirred for 30 minutes
  2. customthe layers were separated
  3. washAqueous layer was washed with EtOAc three times
  4. washAll combined organic layers were washed with brine
  5. dry with materialdried with sodium sulfate
  6. filtrationFiltered
  7. concentrationconcentrated in vacuo
  8. customPurified by silica gel chromatography (0-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-58fbf893efed4b78941cd3312d112788
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

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