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

HRID 1442779Notes

Reaction equation

HRID 1442779 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-4361a02b934347ab806350471e776be1
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

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