Water → N-(3-Nitrophenethyl)acetamide

HRID 1005682Notes

Reaction equation

HRID 1005682 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

In pyridine (33 ml) was dissolved 5.559 g of 3-nitrophenethylamine (Preparation Example 25), followed by dropwise addition of acetyl chloride (2.5 ml) under ice-cooling. After stirring at room temperature for 0.5 hour, the mixture was again ice-cooled. Water was added thereto, followed by extracting with ethyl acetate, The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give the title compound (6.323 g, 91%) as a yellow oil.

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. extractionby extracting 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-ade47436397045c8b8662a77d6fcc02a
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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