Pyrrolidine → 1-(3-Chlorophenyl)-3-(pyrrolidinomethylene)-2(1H,3H)-indolone

HRID 1638470Notes

Reaction equation

HRID 1638470 reaction equation
N1CC[CH2:3][CH2:2]1.[Cl:6][C:7]1[CH:8]=[C:9]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[CH:22][N:23]([CH3:25])[CH3:24])[C:14]2=[O:26])[CH:10]=[CH:11][CH:12]=1>C(O)C>[Cl:6][C:7]1[CH:8]=[C:9]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[CH:22][N:23]3[CH2:24][CH2:3][CH2:2][CH2:25]3)[C:14]2=[O:26])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 537196081-(3-Chlorophenyl)-3-(dimethylaminomethylene)-2(1H,3H)-indolone

Product 1

HCID 544105711-(3-Chlorophenyl)-3-(pyrrolidinomethylene)-2(1H,3H)-indolone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Pyrrolidine (0.42 ml, 5.0 mmoles) was added to a solution of the title product of Example A3 (0.3 g, 1.0 mmole) in 10 ml of ethanol. The mixture was stirred 3 hours and then allowed to stand for 16 hours at 25°. The reaction mixture was evaporated to dryness in vacuo. The residue was triturated with ether and filtered with pentane wash to yield purified title product, 0.253 g; m.p. 108°-112°.

Workup

  1. waitto stand for 16 hours at 25°
  2. customThe reaction mixture was evaporated to dryness in vacuo
  3. customThe residue was triturated with ether
  4. filtrationfiltered with pentane
  5. washwash
  6. customto yield
  7. custompurified title product, 0.253 g

Sources & evidence

ORD record
ord-7edb7cfd71904649baed2f71c4ef5018
Source dataset
uspto-grants-1989_11
Patent number
US04879391

Reaction notes

Loading…