Toluene → 1-(3-Chlorophenyl)-3-(1-benzyl-2-pyrrolidinylidene)-2(1H,3H)-indolone

HRID 1110862Notes

Reaction equation

HRID 1110862 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.O=P(Cl)(Cl)Cl.[Cl:26][C:27]1[CH:28]=[C:29]([N:33]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH2:35][C:34]2=[O:42])[CH:30]=[CH:31][CH:32]=1>C(Cl)Cl>[Cl:26][C:27]1[CH:28]=[C:29]([N:33]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:35](=[C:9]3[CH2:10][CH2:11][CH2:12][N:8]3[CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:34]2=[O:42])[CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 24813Phosphorus oxychlorideHCID 791761-Benzyl-3-pyrrolidoneHCID 112995301-(3-Chlorophenyl)-indolin-2-one

Product 1

HCID 537944421-(3-Chlorophenyl)-3-(1-benzyl-2-pyrrolidinylidene)-2(1H,3H)-indolone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-benzyl-2-pyrrolidone (1.58 ml, 9.85 mmoles) was combined with 2 ml toluene under N2 and cooled to 0°-5°. POCl3 (0.5 ml, 5.9 mmoles) was added and the mixture stirred 30 minutes. Toluene (3 ml) and 1-(3-chloro- phenyl-2(1H,3H)-indolone (1.2 g, 4.92 mmoles) were added and the stirred reaction mixture warmed to 25° for 30 minutes and then to 70°-75° for 18 hours. The reaction mixture was cooled, diluted with 100 ml CH2Cl2, washed with saturated NaHCO3, H2O and brine, dried and concentrated in vacuo to an oil (2.6 g). The oil was chromatographed on silica gel (45×150 mm) using CH2Cl2 as eluant, yielding title product, initially an oil which was crystallized from ether/pentane, 1.04 g (53%), m.p. 72°-75°.

Workup

  1. temperaturecooled to 0°-5°
  2. customthe stirred reaction mixture
  3. temperaturewarmed to 25° for 30 minutes
  4. waitto 70°-75° for 18 hours
  5. temperatureThe reaction mixture was cooled
  6. washwashed with saturated NaHCO3, H2O and brine
  7. customdried
  8. concentrationconcentrated in vacuo to an oil (2.6 g)
  9. customThe oil was chromatographed on silica gel (45×150 mm)

Sources & evidence

ORD record
ord-563af21d5ab64430b657afbf771a5fec
Source dataset
uspto-grants-1990_12
Patent number
US04977178

Reaction notes

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