Sodium Hydroxide → 3-Ethylpyridin-2-amine

HRID 861590Notes

Reaction equation

HRID 861590 reaction equation
C(OC([NH:8][C:9]1[C:14]([CH2:15][CH3:16])=[CH:13][CH:12]=[CH:11][N:10]=1)=O)(C)(C)C.[OH-].[Na+]>Cl.C(O)(=O)C>[CH2:15]([C:14]1[C:9]([NH2:8])=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11117638tert-Butyl (3-ethylpyridin-2-yl)carbamate

Product 1

HCID 110516363-Ethylpyridin-2-amineYield 95.1%

Reagents, catalysts & solvents 1

HCID 22641269Acetate-hydrochloric acidSolvent

Procedure

2-t-Butoxycarbonylamino-3-ethylpyridine (4.9 g, 19.8 mmol) was dissolved in 90 ml of 3N HCl/Acetic acid and stirred for two hours. The solution was neutralized with 2N NaOH to pH 7 and then extracted with ethyl acetate (2×400 ml). The organics were dried over magnesium sulfate and concentrated giving 2.3 g (95%) of a yellowish solid. This solid was used in the next reaction without further purification.

Workup

  1. extractionextracted with ethyl acetate (2×400 ml)
  2. dry with materialThe organics were dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-34176ef7fade4428bb746bdea571ae88
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

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