Sodium Hydroxide → 3-(1-Ethyl-1-methylpropyl)-5-isoxazolamine

HRID 2166189Notes

Reaction equation

HRID 2166189 reaction equation
[C:1]([CH2:3][C:4]([C:6]([CH2:10][CH3:11])([CH3:9])[CH2:7][CH3:8])=O)#[N:2].Cl.[NH2:13][OH:14].[OH-].[Na+]>O>[NH2:2][C:1]1[O:14][N:13]=[C:4]([C:6]([CH2:10][CH3:11])([CH3:9])[CH2:7][CH3:8])[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159096Hexanenitrile, 4-ethyl-4-methyl-3-oxo-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 924023-(1-Ethyl-1-methylpropyl)-5-isoxazolamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 16.5 Kg portion of methyl 2-ethylbutyrate was reacted with 60 Kg of n-butyl lithium, diisopropylamine, and 19.1 Kg of methyl iodide to provide 17.4 Kg of methyl 2-ethyl-2-methylbutyrate. A 7.5 Kg portion of the ester thus formed was reacted with 3.25 Kg of acetonitrile and 5.03 g of sodium hydride in 33 liters of tetrahydrofuran to provide 1-ethyl-1-methylpropyl cyanomethyl ketone. The ketone thus formed was reacted with 4.35 Kg of hydroxylamine hydrochloride and 2.54 Kg of sodium hydroxide in 44 liters of water to provide 5.65 Kg of 5-amino-3-(1-ethyl-1-methylpropyl)isoxazole.

Sources & evidence

ORD record
ord-c8edf1bc2ec04a28a02078f0fb9584c6
Source dataset
uspto-grants-1990_07
Patent number
US04943634

Reaction notes

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