Isopropanol → Ammonia methanol

HRID 639932Notes

Reaction equation

HRID 639932 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([Cl:14])=[C:4]([C:15]#[N:16])[N:3]=1.[CH3:17][C:18]1[N:19]=[CH:20][NH:21][CH:22]=1.C(O)(C)C>CC(=O)OCC.CO>[CH3:8][OH:12].[NH3:3].[Cl:14][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=2)[C:2]([N:21]2[CH:22]=[C:18]([CH3:17])[N:19]=[CH:20]2)=[N:3][C:4]=1[C:15]#[N:16]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 86041274HCID 86041274, compoundHCID 178418800HCID 178418800, compound

Product 2

HCID 21705897Ammonia methanolYield 0%HCID 68518318HCID 68518318, compound

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
150 °C

Procedure

1,4-dichloro-6-methoxyisoquinoline-3-carbonitrile (0.25 g, 0.988 mmol) and 4-methylimidazole (0.324 g 3.951 mmol) and 4 mL isopropanol were taken in a sealed tube and heated at 150° C. for 2 h The resulting white solid was dissolved in hot EA-MeOH and dry loaded on a flash column. Flash chromatography (0% to 6% MeOH—NH3 in EA) gave the titled compound as a white solid.

Workup

  1. customdry

Sources & evidence

ORD record
ord-b3a0441977184bf8bc1abb4689026e82
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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