Propargyl alcohol → 9-Fluoro-2-(hydroxymethyl)pyrazolo[1,5-c]quinazolin-5(6H)-one

HRID 1448194Notes

Reaction equation

HRID 1448194 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[N+:12]=[N-:13].[CH2:14]([OH:17])[C:15]#[CH:16]>CCOCC>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6](=[O:11])[N:12]3[N:13]=[C:15]([CH2:14][OH:17])[CH:16]=[C:5]3[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 7859Propargyl alcoholHCID 178514325HCID 178514325, compound

Product 1

HCID 1357375779-Fluoro-2-(hydroxymethyl)pyrazolo[1,5-c]quinazolin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.0 g (0.0113 mole) of 5-fluoro-3-diazooxindole (part B) and 13.1 g (0.226 mole of 20 equivalents) of 97% propargyl alcohol are refluxed under argon for 4 hours. The reaction mixture is cooled, diluted with ether (200 ml) and stirred for 15 minutes. The beige-colored precipitates are filtered off and dried in vacuo overnight. Yield: 2.3 g, mp 295°-297°, 87.5% crude yield. The crude product is taken up in absolute ethanol (500 ml), treated with activated carbon, filtered through a Celite pad; the pad is washed with 50 ml of hot ethanol. The clear filtrate is concentrated down to a volume of 100 ml and cooled. The white precipitates are filtered off and dried in vacuo at 60° to yield the product (title compound) 1.16 g, mp 303°-304°.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customThe beige-colored precipitates
  3. filtrationare filtered off
  4. customdried in vacuo overnight
  5. additiontreated with activated carbon
  6. filtrationfiltered through a Celite pad
  7. washthe pad is washed with 50 ml of hot ethanol
  8. concentrationThe clear filtrate is concentrated down to a volume of 100 ml
  9. temperaturecooled
  10. customThe white precipitates
  11. filtrationare filtered off
  12. customdried in vacuo at 60°

Sources & evidence

ORD record
ord-f170614a07ba4e8ab1eb924135bcd958
Source dataset
uspto-grants-1979_12
Patent number
US04179561

Reaction notes

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