2-Methyl-5-Nitroaniline → (2-Methyl-5-nitrophenyl)pyrrolidine

HRID 2070341

Reaction equation

HRID 2070341 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH2:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH:20](Br)[CH2:21][CH3:22]>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]1[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 74442-Methyl-5-NitroanilineHCID 107921,2-DibromobutaneHCID 11430Potassium Carbonate

Product 1

HCID 69558510(2-Methyl-5-nitrophenyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To the mixture containing 2-methyl-5-nitrophenylamine and potassium carbonate (4 eq) in dimethyl formamide was added 1,2 dibromobutane (4 eq) and the resulting mixture was stirred at 70° C. for 16 hours. The reaction mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was dried with sodium sulfate and concentrated and purified on silica gel to give (2-methyl-5-nitrophenyl)pyrrolidine.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. concentrationconcentrated
  5. custompurified on silica gel

Sources & evidence

ORD record
ord-94369907dd7b4e7a88b5b3955fb666d3
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Linked notes

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