Aniline → HCID 178418256, compound

HRID 232147Notes

Reaction equation

HRID 232147 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:8]([O-])=O.[Na+].[C:12]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].C([O-])(=O)C.[Na+]>O.Cl.C(O)C>[CH2:19]([O:18][C:12](=[O:17])[C:13](=[N:8][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:14](=[O:15])[CH3:16])[CH3:20]

Participants

8

Reactant 4

HCID 6115AnilineHCID 8868Ethyl AcetoacetateHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178418256HCID 178418256, compoundYield 80,255.703%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of aniline (37.2 g, 0.4 mmol) in water (32 ml) and concentrated hydrochloric acid (100 ml) was poured into ice (400 g). The 0° C. solution was treated with a solution of sodium nitrite (27.6 g, 0.4 mmol) in water (50 ml). The diazonium salt solution was poured rapidly into a stirred solution of ethyl acetoacetate (52 g, 0.4 mmol) in ethanol (300 ml) and ice water (1.0 L) containing sodium acetate (100 g, 1.2 mmol). Th mixture was stirred at 0° C. for 2.5 hours, filtered, and the filter cake was crystallized from ethanol to yield the title compound (75.2 g), m.p. 75°-76° C. (lit 61°-64° C.).

Workup

  1. filtrationfiltered
  2. customthe filter cake was crystallized from ethanol

Sources & evidence

ORD record
ord-76927dd4723a4ec38d9eadc39fa63e08
Source dataset
uspto-grants-1989_07
Patent number
US04851425

Reaction notes

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