Ammonia → 8-Fluoroisoquinoline

HRID 1181401Notes

Reaction equation

HRID 1181401 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]#[C:11][Si](C)(C)C)[C:3]=1[CH:4]=O.CO.[NH3:18]>>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:3]=1[CH:4]=[N:18][CH:11]=[CH:10]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 59536255HCID 59536255, compound

Product 1

HCID 269856658-FluoroisoquinolineYield 58%

Conditions

Temperature
80 °C

Procedure

2-Fluoro-6-[(trimethylsilyl)ethynyl]benzaldehyde Description 40; 10.38 g, 47.1 mmol) was dissolved in 2M ammonia in methanol (235 ml, 471 mmol) in a Parr flask and the resulting mixture heated at 80° C. with shaking on a Parr apparatus (ca. 35 psi achieved). The reaction was cooled and the solvents evaporated. The residue was purified by column chromatography on silica eluting with a gradient from neat dichloromethane to 2% methanol in dichloromethane to give the title compound (4.0 g, 58%).

Workup

  1. temperatureThe reaction was cooled
  2. customthe solvents evaporated
  3. customThe residue was purified by column chromatography on silica eluting with a gradient from neat dichloromethane to 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-11f02a3e3da14eae86d5fe3bbf3b0a67
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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