Methanol → 1-(Hydroxymethyl)-2-phenylpyrazolo[1,5-c]quinazolin-5(6H)-one

HRID 1448159Notes

Reaction equation

HRID 1448159 reaction equation
O=C1[N:11]2[N:12]=[C:13]([CH:21]=O)[C:14]([C:15]3C=CC=CC=3)=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[NH:3]1.[BH4-].[Na+].[OH2:25].[CH3:26][OH:27]>>[OH:25][CH2:15][C:14]1[C:13]([C:21]2[CH:6]=[CH:5][CH:4]=[CH:9][CH:8]=2)=[N:12][N:11]2[C:10]=1[C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:3][C:26]2=[O:27]

Participants

5

Reactant 4

HCID 887Methanol2×HCID 962Water2×HCID 4311764Sodium borohydride2×HCID 1357375705,6-Dihydro-5-oxo-1-phenylpyrazolo[1,5-c]quinazolin-2-carboxaldehyde

Product 1

HCID 1357375661-(Hydroxymethyl)-2-phenylpyrazolo[1,5-c]quinazolin-5(6H)-one

Procedure

To a suspension of 4.0 g (0.0139 mole) of 5,6-dihydro-5-oxo-1-phenylpyrazolo[1,5-c]quinazolin-2-carboxaldehyde (prepared as in Example 1A) in 300 ml of methanol (at 0°) there is added 2.5 g (0.066 mole) of sodium borohydride. The suspension is stirred at 0° for 15 minutes and then overnight at room temperature. Another 2.5 g of sodium borohydride is added, and, after 6 hours another 2.5 g, and stirring continued overnight. The reaction mixture is treated with 200 ml of water, the methanol stripped, the solid (3.7 g) filtered and dried. This material is suspended in 500 ml of absolute ethanol, the mixture cooled to 0°, treated with 2.5 g of sodium borohydride, and stirred for 5 hours at room temperature, after which reduction is complete. The suspension is treated with 250 ml of water and stripped to a low volume. The precipitate is filtered, washed with water and dried (wt. 2.5 g). Recrystallization from absolute ethanol containing 2% benzene gives 2.1 g of analytically pure material, which contains 1 mole of water, m.p. 267°-270° (d).

Workup

  1. customovernight
  2. customat room temperature
  3. waitafter 6 hours another 2.5 g
  4. stirringstirring continued overnight
  5. filtrationthe solid (3.7 g) filtered
  6. customdried
  7. temperaturethe mixture cooled to 0°
  8. additiontreated with 2.5 g of sodium borohydride
  9. stirringstirred for 5 hours at room temperature
  10. additionThe suspension is treated with 250 ml of water
  11. filtrationThe precipitate is filtered
  12. washwashed with water
  13. customdried (wt. 2.5 g)
  14. customRecrystallization from absolute ethanol containing 2% benzene
  15. customgives 2.1 g of analytically pure material, which

Sources & evidence

ORD record
ord-a13c9d6be463430d945154fc51458027
Source dataset
uspto-grants-1979_12
Patent number
US04179561

Reaction notes

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