N-methyl-2-pyrrolidone → HCID 56632142, compound

HRID 1723547Notes

Reaction equation

HRID 1723547 reaction equation
P(Cl)(Cl)(Cl)=O.[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C:7]1=[O:15].[CH3:16][N:17]1[CH2:21][CH2:20][CH2:19][C:18]1=O>>[CH3:16][N:17]1[CH2:21][CH2:20][CH2:19][C:18]1=[C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:6][C:7]1=[O:15]

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidone2×HCID 24813Phosphorus oxychlorideHCID 321710Oxindole

Product 1

HCID 56632142HCID 56632142, compound

Procedure

Under nitrogen, N-methyl-2-pyrrolidone (3 ml) was cooled in an ice-water bath. Phosphorus oxychloride (0.91 ml, 0.01 mole) was added dropwise. After stirring 15 minutes, the bath was removed and 2(1H,3H)-indolone (oxindole, 1.3 g, 0.01 mole) in 3 ml. additional N-methyl-2-pyrrolidone (3 ml) was added dropwise. The temperature rose to 40° C. The reaction mixture was then heated at 80° for 16 hours, cooled and partitioned between ethyl acetate and water. The aqueous layer was washed with fresh ethyl acetate, basified to pH 9 with 6N NaOH and clarified by filtration. The filtrate was extracted with ethyl acetate. The extract was evaporated to dryness and the resulting title product triturated with ethyl acetate, 0.24 g, m.p. 268°-271° C. (dec). See Ind. J. Chem. 12: 940-942 (1974).

Workup

  1. customthe bath was removed
  2. customrose to 40° C
  3. temperatureThe reaction mixture was then heated at 80° for 16 hours
  4. temperaturecooled
  5. custompartitioned between ethyl acetate and water
  6. washThe aqueous layer was washed with fresh ethyl acetate
  7. filtrationclarified by filtration
  8. extractionThe filtrate was extracted with ethyl acetate
  9. customThe extract was evaporated to dryness
  10. customthe resulting title product triturated with ethyl acetate, 0.24 g, m.p. 268°-271° C. (dec)

Sources & evidence

ORD record
ord-987908b5170b49c59c57eabad8946d26
Source dataset
uspto-grants-1989_08
Patent number
US04861880

Reaction notes

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