Hydrochloric Acid → HCID 22667726, compound

HRID 1007101Notes

Reaction equation

HRID 1007101 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[NH:12]1[CH2:19][CH2:18][CH2:17][C@H:13]1[C:14]([OH:16])=[O:15].C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N:12]2[CH2:19][CH2:18][CH2:17][CH:13]2[C:14]([OH:16])=[O:15])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 22667726HCID 22667726, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 4-bromo-2-fluoro-1-nitro-benzene (9 g, 40 mmol), L-proline (4.6 g, 40 mmol), and potassium carbonate (7 g, 50 mmol) in ethanol (50 ml) and water (40 ml) was heated to reflux for 5 hours. After cooling to room temperature, the mixture was diluted with water and was adjusted to pH 6 with 1N aqueous HCl solution. The mixture was extracted with EtOAc (2×100 mL), the combined organic extracts were washed with water, then brine, dried (MgSO4) and evaporated to afford N-(5-bromo-2-nitro-phenyl)-pyrrolidine-2-carboxylic acid (6 g, 48%) which was used in the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. extractionThe mixture was extracted with EtOAc (2×100 mL)
  4. washthe combined organic extracts were washed with water
  5. dry with materialbrine, dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-406a4b9a20cf4f5d96f8679ec17819cb
Source dataset
uspto-grants-2004_09
Patent number
US06794373B2

Reaction notes

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