N-methyl-2-pyrrolidone → 6-Chloro-1-phenyl-3-(1-methyl-2-pyrrolidinylidene)-2(1H,3H)-indolone

HRID 1632648Notes

Reaction equation

HRID 1632648 reaction equation
ClC1C=[C:4]([N:8]2[C:16]3[C:11](=CC=CC=3)[CH2:10][C:9]2=O)C=CC=1.[Cl:18][C:19]1[CH:27]=[C:26]2[C:22]([CH2:23][C:24](=[O:34])[N:25]2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:21][CH:20]=1.CN1CCCC1=O>>[Cl:18][C:19]1[CH:27]=[C:26]2[C:22]([C:23](=[C:9]3[CH2:10][CH2:11][CH2:16][N:8]3[CH3:4])[C:24](=[O:34])[N:25]2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 112995301-(3-Chlorophenyl)-indolin-2-oneHCID 127771686-chloro-1-phenyl-2(1H,3H)-indolone

Product 1

HCID 566264046-Chloro-1-phenyl-3-(1-methyl-2-pyrrolidinylidene)-2(1H,3H)-indolone

Procedure

By the procedure of Example B1 a mixture of 1-(3-chlorophenyl)-2(1H,3H)-indolone and 6-chloro-1-phenyl-2(1H,3H)-indolone (1.36 g, 5.56 mmoles) and N-methyl-2-pyrrolidone (0.9 ml, 9.34 mmoles) were converted to a crude mixture of title products, as an oil. The isomers were separated, purified and isolated as solid products by silica gel chromatography, using the same eluant. The 3-chlorophenyl isomer was the faster moving, yield 0.72 g, m.p. 134°-137°.

Workup

  1. additionmixture of title products
  2. customThe isomers were separated
  3. custompurified
  4. customisolated as solid products by silica gel chromatography

Sources & evidence

ORD record
ord-c6d64fd3b54e4ca3a308ffd0fab234d4
Source dataset
uspto-grants-1984_10
Patent number
US04476307

Reaction notes

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