Hydrochloric Acid → HCID 178516549, compound

HRID 24736Notes

Reaction equation

HRID 24736 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[C:11](Cl)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH2:20].Cl>CN(C)C1C=CN=CC=1.CN(C=O)C>[C:11]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[C:3]([OH:20])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:2]1=[O:10])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7412Benzoyl chlorideHCID 321710Oxindole

Product 1

HCID 178516549HCID 178516549, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
45 °C

Procedure

26.6 g (0.2 mol) of 2-indolinone and 53.8 g (0.44 mol) of 4-dimethylamino-pyridine are dissolved in 400 ml of DMF and after the addition of 30.9 g (0.22 mol) of benzoylchloride in 100 ml of DMF stirred for 45 minutes at 45° C. The solution is poured onto 3 l of water and 100 ml of conc. hydrochloric acid, the precipitate formed is suction filtered, recrystallised from glacial acetic acid and dried.

Workup

  1. customthe precipitate formed
  2. filtrationfiltered
  3. customrecrystallised from glacial acetic acid
  4. customdried

Sources & evidence

ORD record
ord-a7f191f9f60f4495a13277724fab088b
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

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