Sodium Hydroxide → 1-Isopropyl-5-hydroxymethylisoquinoline

HRID 1156911Notes

Reaction equation

HRID 1156911 reaction equation
[CH:1]([C:4]1[C:13]2[C:8](=[C:9]([CH2:14]N)[CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][N:5]=1)([CH3:3])[CH3:2].N([O-])=[O:17].[Na+].[OH-].[Na+]>C(O)(=O)C.O>[CH:1]([C:4]1[C:13]2[C:8](=[C:9]([CH2:14][OH:17])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][N:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 128327661-Isopropyl-5-aminomethylisoquinolineHCID 23668193Sodium Nitrite

Product 1

HCID 128327671-Isopropyl-5-hydroxymethylisoquinolineYield 81.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1-iso-Propyl-5-aminomethylisoquinoline (8.7 g) was dissolved in 20 ml of acetic acid and 20 ml of water, and with ice cooling, 9 g of sodium nitrite was added. The mixture was stirred for 30 minutes. Then, 30 ml of a 10 N aqueous solution of sodium hydroxide was added, and the mixture was heated for 1 hour. The product was extracted with ethyl acetate, washed in water, and dried, followed by distilling off the solvent. Recrystallization of the residue from methylene chloride/n-hexane afforded 7.1 g of 1-isopropyl-5-hydroxymethylisoquinoline as colorless needles having a melting point of 119.9° to 120.9° C.

Workup

  1. temperaturethe mixture was heated for 1 hour
  2. extractionThe product was extracted with ethyl acetate
  3. washwashed in water
  4. customdried
  5. distillationby distilling off the solvent
  6. customRecrystallization of the residue from methylene chloride/n-hexane

Sources & evidence

ORD record
ord-b48387991ab84f44bddf3e912a49ec60
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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