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

HRID 2188906Notes

Reaction equation

HRID 2188906 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8]C(=O)C(C)(C)C)[CH:5]=[C:4]([CH3:15])[CH:3]=1.[OH-].[Na+]>Cl>[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:15])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59165851N-(6-chloro-4-methylpyridin-2-yl)pivalamide

Product 1

HCID 198148426-Chloro-4-methylpyridin-2-amineYield 82%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-(6-chloro-4-methylpyridin-2-yl)pivalamide (500 mg, 2.21 mmol) in HCl (40 mL, 6 M) was stirred for 6 hours at 90° C. The mixture was cooled to room temperature and neutralized with NaOH to pH 10. The mixture was extracted with ethyl acetate, evaporated under vacuum, and purified by chromatography on silica gel (5% ethyl acetate in petroleum ether) to afford 6-chloro-4-methylpyridin-2-amine (257 mg, 82%). 1H NMR (CDCl3, 300 MHz) δ 6.52 (s, 1H), 6.26 (s, 1H), 2.23 (s, 3H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. customevaporated under vacuum
  3. custompurified by chromatography on silica gel (5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-987c49b531514a968a98e0462bb3a2bc
Source dataset
uspto-grants-2012_12
Patent number
US08324207B2

Reaction notes

Loading…