4-Chloro-3-nitroaniline → HCID 85712528, compound

HRID 1872190Notes

Reaction equation

HRID 1872190 reaction equation
[N:1]([O-])=O.[Na+].[Cl:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][C:7]=1[N+:13]([O-:15])=[O:14].CC[C:18](=O)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>O.Cl.C(O)C.[OH-].[K+]>[CH2:23]([O:22][C:20](=[O:21])[C:19](=[N:1][NH:10][C:9]1[CH:11]=[CH:12][C:6]([Cl:5])=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=1)[CH3:18])[CH3:24]

Participants

8

Reactant 3

HCID 124774-Chloro-3-nitroanilineHCID 78656Ethyl 3-oxovalerateHCID 23668193Sodium Nitrite

Product 1

HCID 85712528HCID 85712528, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 14797Potassium HydroxideSolvent

Procedure

To a solution of sodium nitrite (2.17 g, 31 mmol) in water (60 mL) and conc. HCl (12 mL) at 0° C. was added 4-chloro-3-nitroaniline (5.0 g, 29 mmol). After 5 minutes, a solution of ethyl methylacetoacetate (4,5 mL, 29 mmol) in water (60 mL), ethanol (30 mL) and 50% potassium hydroxide (10 mL) was added and the reaction mixture was stirred overnight. The precipitate was collected (7.0 g, 91%).

Workup

  1. customThe precipitate was collected (7.0 g, 91%)

Sources & evidence

ORD record
ord-fcd6a89f288841f99a859480efde9b02
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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