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

HRID 711061Notes

Reaction equation

HRID 711061 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-ed7779a649ff429b94b6f4d39cee6356
Source dataset
uspto-grants-2015_11
Patent number
US09181252B2

Reaction notes

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