Ammonia → 6,8-Difluoro-3-methylisoquinoline

HRID 1181417Notes

Reaction equation

HRID 1181417 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([C:11]#[C:12][CH3:13])[C:3]=1[CH:4]=O.[NH3:14].CO>>[F:10][C:8]1[CH:7]=[C:6]2[C:3](=[C:2]([F:1])[CH:9]=1)[CH:4]=[N:14][C:12]([CH3:13])=[CH:11]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 858697692,4-Difluoro-6-prop-1-ynylbenzaldehyde

Product 1

HCID 691593316,8-Difluoro-3-methylisoquinolineYield 59%

Conditions

Temperature
80 °C

Procedure

A mixture of 2,4-difluoro-6-prop-1-ynylbenzaldehyde (Description 71, 8.7 g; 48.8 mmol) and 2.0M ammonia in methanol (244 ml; 488 mmol) were heated together at 80° C. in a Parr apparatus (approx 35 psi achieved) for 5 hours. The cooled mixture was evaporated and the residue purified by column chromatography on silica-elution with 100% dichloromethane to give the title compound (5.2 g, 59%) as a brown solid.

Workup

  1. customThe cooled mixture was evaporated
  2. customthe residue purified by column chromatography on silica-elution with 100% dichloromethane

Sources & evidence

ORD record
ord-5cd47b0fb6164ab5b519654e0cf512a6
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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