Trimethylsilyldiazomethane → 1-Chloro-4-methoxyisoquinoline

HRID 2361598Notes

Reaction equation

HRID 2361598 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][N:3]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:14]>C(#N)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:14])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 42818821-Chloro-4-hydroxyisoquinoline

Product 1

HCID 222501441-Chloro-4-methoxyisoquinolineYield 46.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-chloroisoquinolin-4-ol (5.0 g, 27.8 mmol) in acetonitrile (50 mL) was added TMS-diazomethane (12.73 g, 111.2 mmol) at 0° C. The reaction mixture was allowed to come to room temperature and stirred for 2 h. Solvent was evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get 1-chloro-4-methoxyisoquinoline (2.5 g, 46.4%) as off-white solid. 1H NMR (400 MHz, CD3OD): δ ppm 8.29-8.17 (m, 2H), 7.97 (s, 1H), 7.91-7.82 (m, 2H), 4.05 (s, 3H); MS: MS m/z 194.7 (M++1).

Workup

  1. customto come to room temperature
  2. customSolvent was evaporated under reduced pressure
  3. customto get crude compound
  4. customThe crude compound was purified by silica gel chromatography

Sources & evidence

ORD record
ord-116be08a1b8f4e37bbd37f4f8dccdcb2
Source dataset
uspto-grants-2014_04
Patent number
US08691757B2

Reaction notes

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