Ammonia → 4-Methylisoquinolin-5-ol

HRID 10575Notes

Reaction equation

HRID 10575 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2N)[CH:5]=[N:4][CH:3]=1.N([O-])=[O:14].[Na+].O.N>S(=O)(=O)(O)O>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[OH:14])[CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 219799844-Methylisoquinolin-5-amineHCID 23668193Sodium Nitrite

Product 1

HCID 219798234-Methylisoquinolin-5-olYield 63.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 4-methyl-5-aminoisoquinoline (869 mg) in concentrated sulfuric acid (8 ml) was added with sodium nitrite (379 mg) with ice cooling and stirring and stirred for 0.5 hours. The reaction mixture was added with water (12 ml) and then stirred at 130° C. for 16 hours. The reaction mixture was neutralized with 28% aqueous ammonia solution and extracted with ethyl acetate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=30:1) to obtain the title compound (559 mg).

Workup

  1. stirringstirred for 0.5 hours
  2. stirringstirred at 130° C. for 16 hours
  3. extractionextracted with ethyl acetate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-390a66a2058b4bf8bb6c50b5617ecc7b
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Reaction notes

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