N-methyl-2-pyrrolidone → HCID 67775458, compound

HRID 533407Notes

Reaction equation

HRID 533407 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1Cl)=[CH:9][C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=2.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.CN1C(=O)CCC1>O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[CH:9][C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 31268PyrrolidineHCID 67773511HCID 67773511, compound

Product 1

HCID 67775458HCID 67775458, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of methyl 3,4-dichloroquinoline-6-carboxylate (100 mg), pyrrolidine (33 mg), and NMP (2 mL) was heated under stirring at 180° C. for 10 minutes under microwave irradiation. The reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate) to obtain methyl 3-chloro-4-(pyrrolidin-1-yl)quinoline-6-carboxylate (40 mg).

Workup

  1. temperaturewas heated
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5626bd27a1474a7683cd928c1ee69468
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

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