1,2-Dichloroethane → HCID 9818690, compound

HRID 1586139Notes

Reaction equation

HRID 1586139 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) is stirred at room temperature overnight. The reaction mixture is stirred with 1 volume of water, made basic with NaOH, and the layers are separated. The basic layer is acidified with acetic acid and the yellow precipitate that forms is collected by filtration, washed with water and dried. The product is 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 are separated
  2. filtrationthe yellow precipitate that forms is collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe product is recrystallized from hot acetonitrile/methanol

Sources & evidence

ORD record
ord-405a393f160a4255831ccc62085e6a7f
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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