Sodium Methoxide → 7-Bromo-3-methoxyisoquinoline

HRID 711100Notes

Reaction equation

HRID 711100 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7](Cl)[N:8]=[CH:9]2)=[CH:4][CH:3]=1.[CH3:13][O-:14].[Na+]>COCCOCCOC.C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([O:14][CH3:13])[N:8]=[CH:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 10942334Sodium MethoxideHCID 513419807-Bromo-3-chloroisoquinoline

Product 1

HCID 674917667-Bromo-3-methoxyisoquinolineYield 87.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8150DiglymeSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 7-bromo-3-chloroisoquinoline (100 mg, 0.4 mmol) and sodium methoxide (113 mg, 2.1 mmol) in diglyme (1 mL) was heated to 150° C. for 1 hour. The reaction was cooled to room temperature and diluted with toluene and water. The layers were separated and the aqueous layer was extracted with toluene (3×). The combined organics were washed with water and brine, dried over sodium sulfate, filtered, and concentrated to an oil. The oil was dried under vacuum overnight to give the title compound (83 mg, 85%) as a yellow solid. +ESI (M+H+1) 240.1; 1H NMR (400 MHz, CDCl3, δ): 8.87 (s, 1H), 8.01-8.05 (m, 1H), 7.58-7.64 (m, 1H), 7.53-7.58 (m, 1H), 6.97 (s, 1H), 4.02 (s, 3H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with toluene (3×)
  4. washThe combined organics were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. customThe oil was dried under vacuum overnight

Sources & evidence

ORD record
ord-22fe6b9afa04446ba9c3a1f590a8d437
Source dataset
uspto-grants-2015_11
Patent number
US09181252B2

Reaction notes

Loading…