Ammonia → 8-Fluoroisoquinoline

HRID 445249Notes

Reaction equation

HRID 445249 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.[NH3:16]>>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:3]=1[CH:4]=[N:16][CH:11]=[CH:10]2

Participants

3

Reactant 2

HCID 222AmmoniaHCID 59536255HCID 59536255, compound

Product 1

HCID 269856658-Fluoroisoquinoline

Conditions

Temperature
80 °C

Procedure

2-Fluoro-6-(2-(trimethylsilyl)ethynyl)benzaldehyde (2.3 g, 10.5 mmol) was dissolved in ammonia (2M in methanol, 15 mL, 30 mmol) and the resulting mixture was heated at 80° C. in a sealed tube for 2.5 h. The solvent was removed under high vacuum and the resulting crude product purified by silica gel chromatography (20-30% EtOAc in hexanes) to give 8-fluoroisoquinoline as a pale yellow solid. MS (ESI, pos. ion) m/z: 148 (M+1).

Workup

  1. customThe solvent was removed under high vacuum
  2. customthe resulting crude product purified by silica gel chromatography (20-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-52cd58a7e16f4c35b03c4399d899e146
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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