Diethyl Ether → N-(3-nitrophenyl)acrylamide

HRID 261360Notes

Reaction equation

HRID 261360 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].C(OCC)C.[C:16](Cl)(=[O:19])[CH:17]=[CH2:18].[OH-].[Na+]>O.C(OCC)(=O)C>[C:16]([NH:7][C:6]1[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:19])[CH:17]=[CH2:18]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 74233-NitroanilineHCID 13140Acryloyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 12531248N-(3-nitrophenyl)acrylamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 13.8 g. (0.10 mol) of m-nitroaniline in 100 ml. of diethyl ether and 30 ml. of ethyl acetate was added 9.0 g. (0.10 mol) of acryloyl chloride and a solution of 4.0 g. (0.10 mol) of sodium hydroxide in 20 ml. of water. The mixture was stirred overnight (18 hours) at ambient temperature and the precipitate filtered to give N-propenoyl-3-nitroaniline.

Workup

  1. filtrationthe precipitate filtered

Sources & evidence

ORD record
ord-835773b9069f4a10aaac51a392a71f7f
Source dataset
uspto-grants-1979_08
Patent number
US04165365

Reaction notes

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