Ethanol → HCID 54191494, compound

HRID 1646218Notes

Reaction equation

HRID 1646218 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+].[CH2:21]([OH:23])[CH3:22].NOS(O)(=O)=O>O>[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14]1=[N:16][N:17]([N:1]=[CH:2][C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[CH:18]=[C:13]1[CH2:12][CH:11]3[CH:21]([C:22]1[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=1)[OH:23])=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 76284hydroxylamine-O-sulfonic acidHCID 10421619HCID 10421619, compound

Product 1

HCID 54191494HCID 54191494, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a warm suspension (50° C.) of 11-amino-4,5-dihydro-1H-pyrazolo[3,4-a]acridine (26.77 g) and solid sodium hydroxide (24.9 g) in water (377 ml) was added ethanol (1133 ml). Hydroxylamine-o-sulfonic acid (34.27 g) was added in portions over 15 minutes and the reaction was cooled to room temperature. The resulting solid was filtered, washed with water, air dried, heated with excess benzaldehyde, filtered to remove insolubles, concentrated, and triturated (diethyl ether) to yield 10.32 g of a mixture of the target product and 11-amino-2-benzylideneamino-4,5-dihydro-2H-pyrazolo[3,4-a]acridine.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with water, air
  3. customdried
  4. temperatureheated with excess benzaldehyde
  5. filtrationfiltered
  6. customto remove insolubles
  7. concentrationconcentrated
  8. customtriturated (diethyl ether)

Sources & evidence

ORD record
ord-f4e2e2274426442da25672e487b14647
Source dataset
uspto-grants-1993_01
Patent number
US05179100

Reaction notes

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