4-Nitrobenzoyl chloride → HCID 22761198, compound

HRID 1703430Notes

Reaction equation

HRID 1703430 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]1([N:19]2[CH2:23][CH2:22][CH:21]([NH2:24])[CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O>[C:13]1([N:19]2[CH2:23][CH2:22][CH:21]([NH:24][C:8](=[O:9])[C:7]3[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 11430Potassium CarbonateHCID 114009521-phenylpyrrolidin-3-amine

Product 1

HCID 22761198HCID 22761198, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of 6.9 g (0.037 mole) of 4-nitrobenzoyl chloride in 30 ml. of chloroform was added dropwise at room temperature to a stirred mixture of 6 g. (0.037 mole) of 1-phenyl-3-aminopyrrolidine and 10 g. of potassium carbonate in 30 ml. of water and 30 ml. of chloroform. The mixture was stirred 30 minutes, the chloroform layer separated, dried over magnesium sulfate and evaporated. Recrystallization of the crude solid residue from alcohol-water gave 10.6 g. (92%) of an orange solid which melted at 153-155° C.

Workup

  1. customthe chloroform layer separated
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customRecrystallization of the crude solid residue from alcohol-water
  5. customgave 10.6 g

Sources & evidence

ORD record
ord-b7025b34942b403d8d953fa54cf5f081
Source dataset
uspto-grants-1978_11
Patent number
USRE029828

Reaction notes

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