2-Acetylbutyrolactone → HCID 13363392, compound

HRID 1980123Notes

Reaction equation

HRID 1980123 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[N:8][CH:9]=1)([O-:3])=[O:2].[C:11]([CH:14]1[CH2:18][CH2:17][O:16][C:15]1=O)(=O)[CH3:12].P(Cl)(Cl)([Cl:22])=O>CC1C=CC=CC=1>[Cl:22][CH2:17][CH2:18][C:14]1[C:15](=[O:16])[N:8]2[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]2=[N:10][C:11]=1[CH3:12]

Participants

5

Reactant 3

HCID 106012-AcetylbutyrolactoneHCID 24813Phosphorus oxychlorideHCID 778882-Amino-5-nitropyridine

Product 1

HCID 13363392HCID 13363392, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 90 parts of 5-nitro-2-pyridinamine, 90 parts of 3-acetyl-4,5-dihydro-2(3H)-furanone and 810 parts of methylbenzene was stirred at room temperature. 510 Parts of phosphoryl chloride were added dropwise during a 1 hour-period: the temperature rose to 40° C. The reaction mixture was heated slowly to reflux and the whole was stirred and refluxed for 5 hours. The solvent was evaporated. The hot residue was poured onto a mixture of crushed ice and ammonium hydroxide. After stirring for 30 minutes, the product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane, yielding 54.8 parts of 3-(2-chloroethyl)-2-methyl-7-nitro-4H-pyrido[1,2-a]pyrimidin-4-one; mp. 170° C. (intermediate 8).

Workup

  1. customrose to 40° C
  2. temperatureThe reaction mixture was heated slowly
  3. temperatureto reflux
  4. stirringthe whole was stirred
  5. temperaturerefluxed for 5 hours
  6. customThe solvent was evaporated
  7. additionThe hot residue was poured onto a mixture of crushed ice and ammonium hydroxide
  8. stirringAfter stirring for 30 minutes
  9. extractionthe product was extracted with trichloromethane
  10. customThe extract was dried
  11. filtrationfiltered
  12. customevaporated
  13. customThe residue was purified by column-chromatography over silica gel using
  14. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  15. customThe pure fractions were collected
  16. customthe eluent was evaporated
  17. customThe residue was crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-aaa0707fbee9463a8612c5172b4a5821
Source dataset
uspto-grants-1984_11
Patent number
US04485107

Reaction notes

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