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

HRID 1649306Notes

Reaction equation

HRID 1649306 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-8afea924be6644c3907c05a4529fe274
Source dataset
uspto-grants-1983_11
Patent number
US04416683

Reaction notes

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