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

HRID 2420881Notes

Reaction equation

HRID 2420881 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-f0782ce4fcd84d29990ca7ee563c9815
Source dataset
uspto-grants-2011_06
Patent number
US07956052B2

Reaction notes

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