Ammonia → 4-Bromo-6-methylpyridin-2-amine

HRID 2307279Notes

Reaction equation

HRID 2307279 reaction equation
Br[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[NH3:10]>>[Br:8][C:6]1[CH:5]=[C:4]([CH3:9])[N:3]=[C:2]([NH2:10])[CH:7]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 126437202,4-Dibromo-6-methylpyridine

Product 1

HCID 226059264-Bromo-6-methylpyridin-2-amine

Conditions

Temperature
160 °C

Procedure

A mixture of 2,4-dibromo-6-methyl-pyridine (J. Bernstein et al., J. Amer. Chem. Soc., 1947, 69, 1147) (22.6 g, 90 mmol) and aqueous ammonia (25%, 260 ml) was stirred in an autoclave at 160° C. for 4 hr. The reaction mixture was cooled to rt and extracted with Et2O. The organic phase was dried (Na2SO4), concentrated and chromatographed (SiO2 with AcOEt/hexane/NEt3=10/30/1) to yield the title compound as a white crystalline material (4.0 g, 6%). NMR (250 MHz, DMSO): δ=3.33 (s, 3H, CH3), 6.13 (s, broad, 2H, NH2), 6.44 (s, 1H, arom-H), 6.54 (s, 1H, arom-H).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionextracted with Et2O
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated
  5. customchromatographed (SiO2 with AcOEt/hexane/NEt3=10/30/1)

Sources & evidence

ORD record
ord-2b0dde5fa98448549c4b41a6839eda32
Source dataset
uspto-grants-2004_12
Patent number
US06831087B2

Reaction notes

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