3-Bromoquinolin-6-amine → 3-Methoxyquinolin-6-amine

HRID 1019970Notes

Reaction equation

HRID 1019970 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([NH2:12])=[CH:7][CH:6]=2.[CH3:13][O-:14].[Na+]>CO.[Cu]>[CH3:13][O:14][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([NH2:12])=[CH:7][CH:6]=2

Participants

5

Reactant 2

HCID 52002663-Bromoquinolin-6-amineHCID 10942334Sodium Methoxide

Product 1

HCID 534257963-Methoxyquinolin-6-amineYield 59.8%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent

Conditions

Temperature
135 °C

Procedure

A suspension of 3-bromo-quinolin-6-ylamine (9.0 g, 40.3 mmol, 1.0 eq), sodium methoxide (10.9 g, 201.7 mmol, 5.0 eq) and copper powder (7.7 g, 121.0 mmol, 3.0 eq) in methanol (240 mL) is heated at 135° C. for 15 hours. The reaction mixture is then filtered and the filtrate is concentrated to give a yellow residue that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate:triethylamine, 2:1:0.05, v/v/v) to afford 3-methoxy-quinolin-6-ylamine as a yellow solid (4.2 g, 59% yield).

Workup

  1. filtrationThe reaction mixture is then filtered
  2. concentrationthe filtrate is concentrated
  3. customto give a yellow residue that
  4. customis purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate:triethylamine, 2:1:0.05, v/v/v)

Sources & evidence

ORD record
ord-6e5a0886fbac4d83829615470d5220c5
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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