2,2-Dimethoxy-1-methylpyrrolidine → 1-(4-Methoxyphenyl)-3-(1-methyl-2-pyrrolidinylidene)-2(1H,3H)-indolone

HRID 1723540

Reaction equation

HRID 1723540 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C:10]2=[O:18])=[CH:5][CH:4]=1.CO[C:21]1(OC)[CH2:25][CH2:24][CH2:23][N:22]1[CH3:26]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[C:21]3[CH2:25][CH2:24][CH2:23][N:22]3[CH3:26])[C:10]2=[O:18])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 110735522,2-Dimethoxy-1-methylpyrrolidineHCID 133395441-(4-Methoxyphenyl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 541264791-(4-Methoxyphenyl)-3-(1-methyl-2-pyrrolidinylidene)-2(1H,3H)-indolone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-(4-Methoxyphenyl)-2(1H,3H)-indolone (49 g, 0.205 mole), N-methyl-2-pyrrolidone dimethyl acetal (ca. 80%, 53 g, 0.245 mole, Ber, 97, pp. 3081-7, 1964) and 1000 ml chloroform were refluxed under nitrogen for 1.5 hours. The reaction mixture was cooled and evaporated in vacuo to solids. Two recrystallizations from ethyl acetate gave purified title product, 44.7 g, m.p. 90°-93° C. Thirty grams of this material were dried at 80° C./15 mm Hg for 20 hours to give 26.1 g of title product, m.p. 127°-9° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated in vacuo to solids
  3. customTwo recrystallizations from ethyl acetate
  4. customgave
  5. custompurified title product, 44.7 g, m.p. 90°-93° C
  6. dry with materialThirty grams of this material were dried at 80° C./15 mm Hg for 20 hours

Sources & evidence

ORD record
ord-b84c88baecb24707a4e1d7024a20efe7
Source dataset
uspto-grants-1989_08
Patent number
US04861880

Linked notes

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