Pyrrolidine → HCID 13354170, compound

HRID 1578263Notes

Reaction equation

HRID 1578263 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1Cl)[N:8]([CH2:13][CH3:14])[CH:7]=[C:6]([C:15]([OH:17])=[O:16])[C:5]2=[O:18].[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[N:8]([CH2:13][CH3:14])[CH:7]=[C:6]([C:15]([OH:17])=[O:16])[C:5]2=[O:18]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 12733886HCID 12733886, compound

Product 1

HCID 13354170HCID 13354170, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6,7-dichloro-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (4.3 g), pyrrolidine (10 cm3) and DMSO (45 cm3) was heated for 2 hours at 110° C. Part of the reaction product precipitated during the reaction. After cooling, it was filtered off and recrystallised from DMF (50 cm3). 3 g of 6-chloro-1-ethyl-4-oxo-7-pyrrolidino-1,4-dihydro-quinoline-3-carboxylic acid, m.p. 325° C., were obtained.

Workup

  1. customPart of the reaction product precipitated during the reaction
  2. temperatureAfter cooling
  3. filtrationit was filtered off
  4. customrecrystallised from DMF (50 cm3)

Sources & evidence

ORD record
ord-325c3fc514ea4eaf8db25871fd690130
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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