Sodium Hydroxide → 2-acetylamino-4-nitrophenyl gamma-N,N-dimethylaminopropyl ether

HRID 1065591Notes

Reaction equation

HRID 1065591 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[OH:14])(=[O:3])[CH3:2].[K].[CH3:16][N:17]([CH3:22])[CH2:18][CH2:19][CH2:20]Cl.[OH-].[Na+]>O.CN(C)C=O>[CH3:16][N:17]([CH2:18][CH2:19][CH2:20][O:14][C:6]1[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]=1[NH:4][C:1](=[O:3])[CH3:2])[CH3:22]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 3292867Acetamide, N-(2-hydroxy-5-nitrophenyl)-HCID 5462222Potassium

Product 1

HCID 205388082-acetylamino-4-nitrophenyl gamma-N,N-dimethylaminopropyl ether

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

35.1 g (0.15 mol) of 2-acetylamino-4-nitrophenol, in the form of the potassium salt, are introduced into 105 ml of dimethylformamide and the mixture is then heated to 60° C., whilst stirring. 25.8 g (0.21 mol) of γ-dimethylaminopropyl chloride are then added; the reaction medium is heated at 90° C. for 210 minutes and is then poured into 750 g of iced water to which 40 ml of 1 N sodium hydroxide solution have been added. The expected product is extracted with methyl isobutyl ketone. After the methyl isobutyl ketone has been driven off in vacuo, the expected product is obtained in the form of an orange oil which crystallises rapidly (melting point: 69° C.).

Workup

  1. temperaturethe reaction medium is heated at 90° C. for 210 minutes
  2. additionhave been added
  3. extractionThe expected product is extracted with methyl isobutyl ketone

Sources & evidence

ORD record
ord-277dccfce98a447c8812d84f6abd7442
Source dataset
uspto-grants-1982_05
Patent number
US04330292

Reaction notes

Loading…