Citric Acid → HCID 609964, compound

HRID 349733Notes

Reaction equation

HRID 349733 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][C:12](=[O:14])[CH3:13].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:3]([NH:11][C:12](=[O:14])[CH3:13])[CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 31268PyrrolidineHCID 2779405N-(2-fluoro-5-nitrophenyl)acetamide

Product 1

HCID 609964HCID 609964, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

0.5 g (2.5 mmol) of N-(2-fluoro-5-nitrophenyl)acetamide was admixed in a pressure reaction vessel with 1 ml (12.6 mmol) of pyrrolidine and stirred at 90° C. for 2.5 hours. After the mixture had been cooled, it was diluted with 20 ml of dichloromethane, adjusted to pH 4 using citric acid solution (10%) and washed four times with water. After the organic phase had been dried, the solvent was removed under reduced pressure. In the aqueous phase, a solid is precipitated out. It was filtered off with suction and washed with water, and combined with the residue from the organic phase (yield 0.58 g, 93%). The product was reacted in stage c without further purification.

Workup

  1. temperatureAfter the mixture had been cooled
  2. washwashed four times with water
  3. customAfter the organic phase had been dried
  4. customthe solvent was removed under reduced pressure
  5. customIn the aqueous phase, a solid is precipitated out
  6. filtrationIt was filtered off with suction
  7. washwashed with water
  8. customThe product was reacted in stage c without further purification

Sources & evidence

ORD record
ord-a3e8ed503ed24238a144129b55c1b3fd
Source dataset
uspto-grants-2007_02
Patent number
US07179941B2

Reaction notes

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