1,2-Dichloroethane → HCID 9818690, compound

HRID 375855Notes

Reaction equation

HRID 375855 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([O:24]C)=[CH:11][CH:10]=3)[CH3:2].B(Br)(Br)Br.ClCCCl.[OH-].[Na+]>O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([OH:24])=[CH:11][CH:10]=3)[CH3:2]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 9884287HCID 9884287, compound

Product 1

HCID 9818690HCID 9818690, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-ethyl-6-methoxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine (5.4 g, 0.016 mol), boron tribromide (48 ml, 0.048 mol) and 1,2-dichloroethane (250 ml) was stirred at room temperature overnight. The reaction mixture was stirred with 1 volume of water, made basic with NaOH and the layers were separated. The basic layer was acidified with acetic acid and the yellow precipitate which formed was collected by filtration, washed with water and dried. The product was recrystallized from hot acetonitrile/methanol to afford 1-ethyl-6-hydroxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, as a yellow powder, m.p. 223°-224° C.

Workup

  1. customthe layers were separated
  2. customthe yellow precipitate which formed
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried
  6. customThe product was recrystallized from hot acetonitrile/methanol

Sources & evidence

ORD record
ord-a0c16e74650a406f9334a121bed5bb82
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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