Hydrazine hydrate (1:1) → 2-amino-N-(2,6-dimethylphenyl)butanamide

HRID 1649989Notes

Reaction equation

HRID 1649989 reaction equation
C1(=O)[N:5]([CH:6]([CH2:18][CH3:19])[C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:17])=[O:8])C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][CH:6]([CH2:18][CH3:19])[C:7]([NH:9][C:10]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:17])=[O:8]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19855569N-(2-phthalimido-butyryl)-2,6-dimethyl-aniline

Product 1

HCID 104205332-amino-N-(2,6-dimethylphenyl)butanamideYield 87.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 17.7 g (52.6 mmoles) of N-(2-phthalimido-butyryl)-2,6-dimethyl-aniline, 14.2 ml of a 85% aqueous hydrazine hydrate solution and 250 ml of ethanol is boiled for one hour, and then the mixture is processed as described in Example 11. The product is triturated with petroleum ether. 9.45 g of N-(2-amino-butyryl)-2,6-dimethyl-aniline are obtained; m.p.: 48°-49° C. The product is obtained with a yield of 87.1%. The hydrochloride of the compound melts at 213°-214° C. [the melting point reported in the literature (see E. W. Byrnes et al., loc. cit.) is 213.5°-214.5° C⟧

Workup

  1. customThe product is triturated with petroleum ether

Sources & evidence

ORD record
ord-44e8dc4069d44a56aab72aad1db97a26
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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