Water → HCID 13156258, compound

HRID 851690Notes

Reaction equation

HRID 851690 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[N:14]([CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.C[O:23][C:24]([CH2:26][CH2:27][C:28](Cl)=[O:29])=[O:25].O>C1C=CC=CC=1>[C:1]1([C:7]2[CH:8]=[C:9]3[N:14]([C:15]=2[C:28](=[O:29])[CH2:27][CH2:26][C:24]([OH:25])=[O:23])[CH:13]=[CH:12][CH:11]=[CH:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 961282-Phenylindolizine

Product 1

HCID 13156258HCID 13156258, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 10.2 g of 2-phenylindolizine in 150 ml of benzene were added 6 ml of pyridine and 9.6 g of β-methoxycarbonylpropionyl chloride and the mixture was refluxed overnight. After cooling, 50 ml of water was added and the whole mixture was extracted with benzene. After the extract was decolorized and concentrated, to the residue was added 30 ml of isopropyl ether and the mixture was cooled to precipitate methyl 4-(2-phenyl-3-indolizinyl)-4-oxobutyrate. The precipitate was filtered off and then this ester compound was hydrolyzed in a conventional manner to give 8.3 g of 4-(2-phenyl-3-indolizinyl)-4-oxobutyric acid, melting at 131°-133° C.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. temperatureAfter cooling
  3. extractionthe whole mixture was extracted with benzene
  4. concentrationconcentrated, to the residue
  5. additionwas added 30 ml of isopropyl ether
  6. temperaturethe mixture was cooled
  7. customto precipitate methyl 4-(2-phenyl-3-indolizinyl)-4-oxobutyrate
  8. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-5583c7c38b9545e2ab77fc2ce41b9c5b
Source dataset
uspto-grants-1983_05
Patent number
US04386092

Reaction notes

Loading…