Benzyl Bromide → HCID 10426535, compound

HRID 1646215Notes

Reaction equation

HRID 1646215 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.[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[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]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:18]=[C:13]1[CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10421619HCID 10421619, compound

Product 1

HCID 10426535HCID 10426535, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 11-amino-4,5-dihydro-1H-pyrazolo[3,4-a]acridine (2.36 g) in dry DMF (90 ml) was added NaH (60%)(0.50 g) slowly. The reaction was stirred at room temperature for 15 minutes and then benzyl bromide (1.88 g) was added and the reaction was stirred an additional 15 minutes. At the end of this time the product was precipitated with water, filtered off, washed well with water, and air dried to yield a product which was further purified by flash chromatography (5% Et3N-EtOAc). The product-containing fractions were combined, concentrated, and recrystallized from EtOAc to give 2.35 g, mp 206°-207°.

Workup

  1. stirringthe reaction was stirred an additional 15 minutes
  2. customAt the end of this time the product was precipitated with water
  3. filtrationfiltered off
  4. washwashed well with water, and air
  5. customdried
  6. customto yield a product which
  7. customwas further purified by flash chromatography (5% Et3N-EtOAc)
  8. concentrationconcentrated
  9. customrecrystallized from EtOAc
  10. customto give 2.35 g, mp 206°-207°

Sources & evidence

ORD record
ord-93f7926f45384f12a64009d6c10eb067
Source dataset
uspto-grants-1993_01
Patent number
US05179100

Reaction notes

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