Hydrochloric Acid → 2-(Hydroxyphenylmethyl)pyrazolo[1,5-c]quinazolin-5(6H)-one

HRID 616932Notes

Reaction equation

HRID 616932 reaction equation
[C:1]([C:9]1[CH:21]=[C:20]2[N:11]([C:12](=[O:22])[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=32)[N:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>C(O)C.O>[OH:8][CH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[CH:21]=[C:20]2[N:11]([C:12](=[O:22])[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=32)[N:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 1357375902-Benzoylpyrazolo[1,5-c]quinazolin-5(6H)-one

Product 1

HCID 1357375912-(Hydroxyphenylmethyl)pyrazolo[1,5-c]quinazolin-5(6H)-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

1.65 g 80.0057 mole) of 2-benzoylpyrazolo[1,5-c]-quinazolin-5(6H)-one prepared as in part B above is stirred with 880 mg (4 equiv) of sodium borohydride in absolute ethanol (125 ml) at room temperature for 3 hours. The reaction mixture is stripped to dryness and the resulting solid is suspended in water (40 ml), cooled down to 0° and treated dropwise with 1 N HCl 25 ml). The mixture is stirred for 30 minutes, diluted with water (40 ml) and stirred for another 10 minutes. The white precipitates are filtered off, washed well with water and dried overnight in a vacuum oven at 70° C to give 1.6 g of product.

Workup

  1. temperaturecooled down to 0°
  2. stirringstirred for another 10 minutes
  3. customThe white precipitates
  4. filtrationare filtered off
  5. washwashed well with water
  6. customdried overnight in a vacuum oven at 70° C

Sources & evidence

ORD record
ord-b65d70e31af048b0bde2c0e6b3ee36a0
Source dataset
uspto-grants-1978_02
Patent number
US04076818

Reaction notes

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