Benzoyl chloride → 5-Benzoyl-1,3-dihydro-2H-indol-2-one

HRID 442532Notes

Reaction equation

HRID 442532 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][C:15]1=[O:23]>>[C:5]([C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[NH:14][C:15](=[O:23])[CH2:16]2)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 7412Benzoyl chlorideHCID 321710OxindoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 134081645-Benzoyl-1,3-dihydro-2H-indol-2-one

Conditions

Temperature
185 °C

Procedure

A stirred slurry of 66 g. (0.5 mole) of aluminum chloride and 42.5 g. (0.3 mole) of benzoyl chloride was heated to 150° C. and then 133 g. (0.1 mole) of indolin-2-one was slowly added at a rate so that the temperature of the stirred reaction mixture was maintained at 180°-185° C. After addition the reaction mixture was stirred for five minutes at 185° C., cooled and poured into ice water. The 5-benzoylindolin-2-one which precipitated was collected and recrystallized from methanol; it melted at 204°-205° C. The yield was 17.5 g. (73%).

Workup

  1. temperaturewas maintained at 180°-185° C
  2. additionAfter addition the reaction mixture
  3. temperaturecooled
  4. customThe 5-benzoylindolin-2-one which precipitated
  5. customwas collected
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-7fc7db9fb41949d0af09bbe09b8c3c8a
Source dataset
uspto-grants-1977_08
Patent number
US04045576

Reaction notes

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