Sodium Methoxide → 6-Methoxyisoquinolin-3-amine

HRID 1672489Notes

Reaction equation

HRID 1672489 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([NH2:12])=[CH:5]2.[CH3:13][O-:14].[Na+]>CS(C)=O>[CH3:13][O:14][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([NH2:12])=[CH:5]2

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 457898316-Bromoisoquinolin-3-Amine

Product 1

HCID 233211576-Methoxyisoquinolin-3-amineYield 53.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

In a dry box, to the microwave test tube (20 ml volume) was added the 6-bromoisoquinolin-3-amine (1.0 g, 4.5 mmol) and the NaOMe (242.0 mg, 4.5 mmol) in 10 ml of DMSO. The microwave test tube was capped and moved from the dry box. The test tube was place into Microwave station to heat at 150° C. for 30 min. The crude residue was purified by a silica gel column to give 420 mg (yield 53.8%). 1H NMR (400 MHz, DMSO-d6) ppm 2.44 (s, 3H), 7.94-8.11 (m, 2H), 8.17 (d, J=8.56 Hz, 2H), 8.82 (s, 1H). MS m/z, (APCI); 175.1 ([M+H]+).

Workup

  1. customThe microwave test tube was capped
  2. customThe crude residue was purified by a silica gel column
  3. customto give 420 mg (yield 53.8%)

Sources & evidence

ORD record
ord-c0131fccd61f454cb679a478741c61f2
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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