Water → 2-Chloro-6-nitro-3-pyrrolidinobenzonitrile

HRID 64861Notes

Reaction equation

HRID 64861 reaction equation
[Cl:1][C:2]1[C:9](Cl)=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]#[N:5].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.O>CN(C)C=O>[Cl:1][C:2]1[C:9]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 27360202,3-Dichloro-6-nitrobenzonitrile

Product 1

HCID 134992682-Chloro-6-nitro-3-pyrrolidinobenzonitrileYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

13.0 g of 2,3-dichloro-6-nitrobenzonitrile was dissolved in 50 ml of dimethylformamide, and 11.0 g of pyrrolidine was added to the solution, followed by stirring while externally cooling because of heat generation. After continuing the stirring for 30 minutes, the reaction mixture was poured into water. The precipitate thus formed was filtered, washed with water and then with methanol to obtain 13.3 g of 2-chloro-6-nitro-3-pyrrolidinobenzonitrile (melting point: 170°-173° C.).

Workup

  1. temperaturewhile externally cooling because of heat generation
  2. customstirring for 30 minutes
  3. customThe precipitate thus formed
  4. filtrationwas filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-25bd0f96e9344708b7d10565fea58a47
Source dataset
uspto-grants-1986_09
Patent number
US04610987

Reaction notes

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