7-Bromo-1-Chloroisoquinoline → 7-Bromo-1-methoxyisoquinoline

HRID 880936Notes

Reaction equation

HRID 880936 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2Cl)=[CH:4][CH:3]=1.[CH3:13][O-:14].[Na+]>CO>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[O:14][CH3:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65020247-Bromo-1-ChloroisoquinolineHCID 10942334Sodium Methoxide

Product 1

HCID 674916117-Bromo-1-methoxyisoquinolineYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

7-Bromo-1-chloroisoquinoline (570 mg, 2.4 mmol) was combined with methanol (10 mL) and sodium methoxide (25 wt % in methanol, 1.5 mL, 24 mmol) in a microwave vial. The vial was sealed and heated to 130° C. for 3 hours in a microwave. The reaction was concentrated. The crude residue was taken up in ethyl acetate and washed with water and saturated aqueous sodium bicarbonate. The aqueous layer was extracted two times with hot ethyl acetate. The combined organics were dried over sodium sulfate, filtered, and concentrated to give the title compound (520 mg, 93%). +ESI (M+H+1) 240.0; 1H NMR (400 MHz, DMSO-d6, δ): 8.25-8.28 (m, 1H), 8.04 (d, J=5.9 Hz, 1H), 7.86-7.89 (m, 2H), 7.40 (dd, J=6.0, 0.9 Hz, 1H), 4.03 (s, 3H).

Workup

  1. customThe vial was sealed
  2. concentrationThe reaction was concentrated
  3. washwashed with water and saturated aqueous sodium bicarbonate
  4. extractionThe aqueous layer was extracted two times with hot ethyl acetate
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5edc0d42ee3d4016870b5f4de29334fa
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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