1-Chloro-4-nitrobenzene → HCID 16769874, compound

HRID 450069Notes

Reaction equation

HRID 450069 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[NH:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14].C(N(CC)CC)C>CS(C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:18][CH2:17][CH2:16][CH:12]2[C:13]([OH:15])=[O:14])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 8471TriethylamineHCID 145742L-Proline

Product 1

HCID 16769874HCID 16769874, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-chloro-4-nitrobenzene (3 g, 19 mmol), L-proline (2.19 g, 19.0 mmol) and triethylamine (10.6 ml, 76 mmol) were dissolved in DMSO (15 ml) then heated at 90° C. for 24 hr. The reaction mixture was concentrated under reduced pressure, the residue treated with water and extracted with dichloromethane. The organic layer was washed with brine, dried and evaporated to a residue. Purification by column chromatography using dichloromethane/methanol (97:3) gave 1-(4-nitro-phenyl)-pyrrolidine-2-carboxylic acid (0.9 g, 20%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue treated with water
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with brine
  5. customdried
  6. customevaporated to a residue
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-16bbfca935a546ad851d8cc6c1dd4adf
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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