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

HRID 537136Notes

Reaction equation

HRID 537136 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-dea21a31665d4ae1a139ad5a651f73d6
Source dataset
uspto-grants-2014_10
Patent number
US08859773B2

Reaction notes

Loading…