Aniline → 2-anilinoacetophenone

HRID 1974433Notes

Reaction equation

HRID 1974433 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11]>C(O)C>[NH:1]([CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 6259Phenacyl bromide

Product 1

HCID 11326242-anilinoacetophenoneYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
22 °C

Procedure

To a solution of 102.44 grams (1.1 mol) of aniline in 500 mL of absolute ethanol stirring at 22° C. was added 99.52 grams (0.5 mol) of 2-bromoacetophenone while maintaining a reaction temperature of 22° C. The reaction was stirred for 1.5 hours at 22° C. during which time a light yellow precipitate formed. The crude product mixture was diluted with 200 mL of ethanol and the precipitated product was collected on a Buchner funnel and washed with 3×200 mL of ethanol, 1×200 mL water, and again 1×200 mL ethanol. The crude product was dried to afford 56.9 grams (0.27 mol, 54% yield) of 2-anilinoacetophenone, m. p.=98°-101° C.

Workup

  1. customformed
  2. customthe precipitated product was collected on a Buchner funnel
  3. washwashed with 3×200 mL of ethanol, 1×200 mL water, and again 1×200 mL ethanol
  4. dry with materialThe crude product was dried

Sources & evidence

ORD record
ord-912dc07a06b6409c893f7068dc620752
Source dataset
uspto-grants-1994_02
Patent number
US05283165

Reaction notes

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