HCID 69596756, compound → HCID 73115471, compound

HRID 1357110Notes

Reaction equation

HRID 1357110 reaction equation
C([NH:4][C:5]([CH2:16][CH2:17][C:18](=O)[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)(C(OCC)=O)[C:6]([O:8][CH2:9]C)=[O:7])(=O)C>Cl>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]2[CH2:17][CH2:16][CH:5]([C:6]([O:8][CH3:9])=[O:7])[N:4]=2)=[CH:20][CH:21]=1

Participants

3

Reactant 1

HCID 69596756HCID 69596756, compound

Product 1

HCID 73115471HCID 73115471, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred solution of diethyl acetamido[2-(4-fluorobenzoyl)-ethyl]malonate (5.72 g, 15.6 mmol) in conc. hydrochloric acid (45 ml) was heated under reflux conditions for 15 h, filtered and evaporated. Subsequently hydrochloric acid in MeOH (3N, 30 ml) was added and the solution stirred at room temperature for 20 h. The reaction mixture was evaporated, sat. NaHCO3 solution was added (50 ml) and the aqueous phase was extracted with ethyl acetate (2×100 ml). The combined organic layers were washed with brine (70 ml), dried (MgSO4) and evaporated to give methyl (RS)-2-(4-fluorophenyl)-1-pyrroline-5-carboxylate (2.3 g, yield 67%) as a pale brown oil, MS: m/e=221 (M+).

Workup

  1. filtrationfiltered
  2. customevaporated
  3. additionSubsequently hydrochloric acid in MeOH (3N, 30 ml) was added
  4. customThe reaction mixture was evaporated
  5. additionsat. NaHCO3 solution was added (50 ml)
  6. extractionthe aqueous phase was extracted with ethyl acetate (2×100 ml)
  7. washThe combined organic layers were washed with brine (70 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-52606b4e9be94eeab7a0fb7cb4eec25f
Source dataset
uspto-grants-2003_07
Patent number
US06589978B2

Reaction notes

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