Chloroacetone → 1-(3-Amino-benzofuran-2-yl)-ethanone

HRID 869371Notes

Reaction equation

HRID 869371 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C([O-])([O-])=O.[K+].[K+].Cl[CH2:17][C:18](=[O:20])[CH3:19]>CN(C=O)C>[NH2:5][C:4]1[C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[O:1][C:17]=1[C:18](=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 119072-Hydroxybenzonitrile

Product 1

HCID 6540951-(3-Amino-benzofuran-2-yl)-ethanoneYield 63.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-hydroxy-benzonitrile (1000 mmol) in DMF (dimethylformamide, 80 mL) was added K2CO3 (207 g, 1.5 mol) portionwise under stirring, followed by 1-chloro-propan-2-one (139 g, 1.5 mol). After addition, the mixture was heated to 120° C. and stirred at that temperature for 2 hours. TLC showed the reaction was completed. The reaction mixture was cooled to room temperature and filtered. The filtrate was extracted with ethyl acetate, washed with brine, dried and concentrated. The residue was washed with dichloromethane, filtered and dried to give 112 g of 1-(3-amino-benzofuran-2-yl)-ethanone (1A).

Workup

  1. additionAfter addition
  2. stirringstirred at that temperature for 2 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washwashed with brine
  7. customdried
  8. concentrationconcentrated
  9. washThe residue was washed with dichloromethane
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-a8db5cf615524903868b0f7f0e7716d2
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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