Dichloromethane → 6-Ethylpyridin-2-amine

HRID 2358539Notes

Reaction equation

HRID 2358539 reaction equation
C(OC(=O)C(=C[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=1)C(OCC)=O)C.Cl.NO.[OH-].[Na+].[CH2:26](Cl)Cl>CCO.O>[CH2:19]([C:15]1[N:14]=[C:13]([NH2:12])[CH:18]=[CH:17][CH:16]=1)[CH3:26]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 83264Diethyl [[(6-methyl-2-pyridyl)amino]methylene]malonateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 890216-Ethylpyridin-2-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

The product from Example 1a (4.93 g, 0.025 mol) was dissolved in a mixture of EtOH (80 mL) and water (30 mL). To this was added hydroxylamine hydrochloride (8.6 g, 0.123 mol) and the resulting mixture heated to 100° C. for 8 h. The reaction mixture was poured into dilute sodium hydroxide solution and the crude product isolated by extraction with CH2Cl2 and dried over MgSO4 filtered and concentrated under vacuum giving the title compound. The material was used as isolated.

Workup

  1. dry with materialdried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f36e7df651844db890fe732531aafe51
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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