Réaction #6041

ord-7032a768e4ff40098e40773662a0af2f

Équation de réaction

O=C([O-])O.[Na+]
NaHCO3
Cl.NNc1ccc(F)cc1
1-(4-fluorophenyl)hydrazine hydrochloride
CCOC(=O)CCC(=O)CC
ethyl 4-oxo-hexanoate
O=S(=O)(O)O
H2SO4
→
Cc1c(CCC(=O)OC(C)C)[nH]c2ccc(F)cc12
isopropyl 5-fluoro-3-methyl-1H-indole-2-propanoate

Réactifs

O=C([O-])O.[Na+]
NaHCO3
Cl.NNc1ccc(F)cc1
1-(4-fluorophenyl)hydrazine hydrochloride
CCOC(=O)CCC(=O)CC
ethyl 4-oxo-hexanoate
O=S(=O)(O)O
H2SO4

Réactifs

Aucun

Solvants

CC(C)O
2-propanol

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températureis refluxed under nitrogen for 9 hours
  2. 2
    TempératureAfter cooling the mixture
  3. 3
    Extractionextracted with AcOEt
  4. 4
    Autreevaporated to dryness

Mode opératoire

A mixture of 1-(4-fluorophenyl)hydrazine hydrochloride (1.03 g), ethyl 4-oxo-hexanoate (1.0 g), 2-propanol (25 ml) and H2SO4 is refluxed under nitrogen for 9 hours. After cooling the mixture is poured into a aqueous solution of NaHCO3, extracted with AcOEt and evaporated to dryness to yield 1.45 g of isopropyl 5-fluoro-3-methyl-1H-indole-2-propanoate.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05246957uspto-grants-1993_09