Water → N-(3-Nitrophenethyl)acetamide

HRID 1173125Notes

Reaction equation

HRID 1173125 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][CH2:8][NH2:9])([O-:3])=[O:2].[C:13](Cl)(=[O:15])[CH3:14].O>N1C=CC=CC=1>[C:13]([NH:9][CH2:8][CH2:7][C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 129500662-(3-Nitrophenyl)ethan-1-amine

Product 1

HCID 22674066N-(3-Nitrophenethyl)acetamideYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Nitrophenethylamine (5.559 g, Production Example 25b) was dissolved in pyridine (33 ml), and acetyl chloride (2.5 ml) was added dropwise thereinto under ice-cooling. After stirring at room temperature for 0.5 hr, the mixture was ice-cooled again. Water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, to give the title compound (6.323 g, 91%) as a yellow oil.

Workup

  1. temperatureunder ice-cooling
  2. temperaturecooled again
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7260cf56fccf496ba7bdd8d0ba480c03
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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