Sodium Hydroxide → HCID 10422267, compound

HRID 1646217Notes

Reaction equation

HRID 1646217 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14]1[NH:16][N:17]=[CH:18][C:13]=1[CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[OH-].[Na+].[NH2:21]OS(O)(=O)=O>C(O)C>[NH2:21][N:17]1[CH:18]=[C:13]2[CH2:12][CH2:11][C:10]3[C:15]([C:14]2=[N:16]1)=[C:2]([NH2:1])[C:3]1[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=1)[N:9]=3

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76284hydroxylamine-O-sulfonic acidHCID 10421619HCID 10421619, compound

Product 1

HCID 10422267HCID 10422267, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

To a suspension of 11-amino-4,5-dihydro-1H-pyrazolo[3,4-a]acridine (40.0 g) in an aqueous sodium hydroxide solution (37.1 g in 561 ml of water) at 50° C. was added ethanol (1550 ml). The resulting solution was heated to 55° C. and solid hydroxylamine-o-sulfonic acid (51.6 g) was added in portions over 15 minutes. The reaction was stirred for a half hour without heat, the resulting solid was filtered, washed with water, boiled in methanol (1500 ml), filtered hot to remove inorganics, concentrated, and triturated with diethyl ether to yield 5.79 g of a product containing approximately 20% of the starting material which was inseparable by chromatography.

Workup

  1. temperaturewithout heat
  2. filtrationthe resulting solid was filtered
  3. washwashed with water
  4. filtrationfiltered hot
  5. customto remove inorganics
  6. concentrationconcentrated
  7. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-1b3b734410a4417b93202dc02c627a11
Source dataset
uspto-grants-1993_01
Patent number
US05179100

Reaction notes

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