4-Nitroaniline → HCID 178472851, compound

HRID 232141Notes

Reaction equation

[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:11]([O-])=O.[Na+].[C:15]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:16][C:17]([CH3:19])=[O:18].C([O-])(=O)C.[Na+]>O.Cl.C(O)C>[CH2:22]([O:21][C:15](=[O:20])[C:16](=[N:11][NH:8][C:7]1[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[C:17](=[O:18])[CH3:19])[CH3:23]

Participants

Conditions

Temperature: -2 °C

Procedure

A suspension of 4-nitroaniline (41.43 g, 0.3 mmol) in water (150 ml) and 37% hydrochloric acid (75 ml) was heated to dissolution. The cooled suspension of hydrochloride salt was treated with sodium nitrite (20.7 g) at -5° C. at a rate which maintained the reaction temperature at -2° C. The diazonium salt solution was added to a solution of ethyl acetoacetate (39 g, 0.3 mmol) in ethanol (225 ml) and ice water (1.5 L) containing sodium acetate (75 g, 0.9 mmol). The mixture thickened and sufficient water was added to permit agitation for 3.5 hours. The mixture was filtered, the filter cake washed with water, and crystallized from ethanol to yield the title compound, (79.16 g), m.p. 128° C.

Workup

temperaturewas heated to dissolution
customfor 3.5 hours
filtrationThe mixture was filtered
washthe filter cake washed with water
customcrystallized from ethanol

Sources & evidence

ORD record: ord-eac6713cdb974feca9ea6d39610abe86
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04851425

Reaction notes

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