Water → HCID 57139336, compound

HRID 965534Notes

Reaction equation

HRID 965534 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH:12]1([CH:18]=O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.N1CCCC1.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:18][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 16275CyclohexanecarboxaldehydeHCID 31268PyrrolidineHCID 1528015-Chlorooxindole

Product 1

HCID 57139336HCID 57139336, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 10 g of 5-chloro-1,3-dihydroindol-2-one, 6.18 g of cyclohexanecarboxaldehyde and 4.93 ml of pyrrolidine in 250 ml of toluene is refluxed for 1 hour, the water formed being removed by means of a Dean-Stark apparatus. The reaction mixture is concentrated to about 90 ml and left to crystallize. The crystalline product formed is filtered off and washed with toluene and then with iso ether to give 9.7 g of the expected product after recrystallization from toluene. M.p.=203°-204° C.

Workup

  1. custombeing removed by means of a Dean-Stark apparatus
  2. concentrationThe reaction mixture is concentrated to about 90 ml
  3. waitleft
  4. customto crystallize
  5. customThe crystalline product formed
  6. filtrationis filtered off
  7. washwashed with toluene

Sources & evidence

ORD record
ord-f546546e23aa4039912f3ae13550b381
Source dataset
uspto-grants-1998_06
Patent number
US05773612

Reaction notes

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