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

HRID 869885Notes

Reaction equation

HRID 869885 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-8c598bf1dba74054b18e5b737d75b9fb
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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