Ammonium Hydroxide → 6-Chloro-4-methylpyridin-2-amine

HRID 2382775Notes

Reaction equation

HRID 2382775 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4](Cl)[N:3]=1.[OH-].[NH4+:11]>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([NH2:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 108989972,6-Dichloro-4-methylpyridine

Product 1

HCID 198148426-Chloro-4-methylpyridin-2-amineYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,6-Dichloro-4-methylpyridine (Chem. Mater., 2004, 16, 1564-1572, 30 g, 0.185 mol) in ammonium hydroxide (200 mL, 25% solution in water) was heated at 200° C. in a pressure vessel for 10 h. The reaction mixture was then concentrated under reduced pressure. The brown solid obtained was suspended in DCM for 30 min at 25-26° C. and filtered. Filtrate was concentrated under reduced pressure. Purification of the crude thus obtained by flash chromatography (20% ethyl acetate in pet ether) afforded the title compound as off-white solid (13.5 g, Yield 51%). LC/MS: M+(ESI): 142.7; 1H NMR (DMSO d6: 400 MHz) δ 6.34 (1H, s), 6.23 (2H, s), 6.15 (1H, s), 2.1 (3H, s).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe brown solid obtained
  3. filtrationfiltered
  4. concentrationFiltrate was concentrated under reduced pressure
  5. customPurification of the crude
  6. customthus obtained by flash chromatography (20% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-f6f1b5ab73b447279b2f1ca24298732c
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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