Water → 3-Chloro-N,N-dimethyl-4-(2-nitrobut-1-en-1-yl)aniline

HRID 1973277Notes

Reaction equation

HRID 1973277 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([N:10]([CH3:12])[CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[N+:13]([CH2:16][CH2:17][CH3:18])([O-:15])=[O:14].C([O-])(=O)C.[NH4+].O>C(O)CC>[CH3:11][N:10]([CH3:12])[C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[C:16]([N+:13]([O-:15])=[O:14])[CH2:17][CH3:18])=[C:2]([Cl:1])[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79031-NitropropaneHCID 74021Benzaldehyde, 2-chloro-4-(dimethylamino)-HCID 517165Ammonium Acetate

Product 1

HCID 537698413-Chloro-N,N-dimethyl-4-(2-nitrobut-1-en-1-yl)aniline

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A solution of 36.8 g of 2-chloro-4-dimethylaminobenzaldehyde, 25 ml of 1-nitropropane and 20 g of ammonium acetate in 150 ml of 1-propanol is refluxed for 15 hours. The mixture is then poured into 1.5 l of water whereupon the compound separates as a viscous red oil. Recrystallization twice from aqueous acetic acid yields 5.0 g of the compound, melting at 90°-91°.

Workup

  1. customRecrystallization twice from aqueous acetic acid

Sources & evidence

ORD record
ord-5cd59fdbbb5d499e831ee925c4e442b0
Source dataset
uspto-grants-1976_12
Patent number
US03996381

Reaction notes

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