6-Bromo-4-methoxypyridin-2-amine → 6-Amino-4-methoxypicolinonitrile

HRID 1696754Notes

Reaction equation

HRID 1696754 reaction equation
Br[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([O:9][CH3:10])[CH:3]=1.[Cu][C:12]#[N:13]>CN(C)C=O>[NH2:8][C:6]1[N:7]=[C:2]([C:12]#[N:13])[CH:3]=[C:4]([O:9][CH3:10])[CH:5]=1

Participants

4

Reactant 2

HCID 714642286-Bromo-4-methoxypyridin-2-amineHCID 178418546HCID 178418546, compound

Product 1

HCID 552848206-Amino-4-methoxypicolinonitrileYield 29.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
220 °C

Procedure

To a solution of 0.40 g 6-bromo-4-methoxy-pyridin-2-ylamine in 8.0 ml dimethylformamide was added 0.265 g copper(I) cyanide and the mixture was heated to 220° C. under microwave irradiation for 6 min. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and washed with water and brine, dried over magnesium sulfate dihydrate and purified by chromatography on silica gel with heptane : ethyl acetate to yield 0.086 g of the title compound as greenish solid MS (ISP) M+H+=183.1

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customThe phases were separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate dihydrate
  5. custompurified by chromatography on silica gel with heptane

Sources & evidence

ORD record
ord-8ce4d24ff6b14d868002dbdb90171ead
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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