Ethanol → HCID 21217692, compound

HRID 1586170Notes

Reaction equation

HRID 1586170 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]([C:24]([O:26]C)=[O:25])=[CH:11][CH:10]=3)[CH3:2].C(O)C.[OH-].[K+]>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[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([C:24]([OH:26])=[O:25])=[CH:11][CH:10]=3)[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 21217691HCID 21217691, compound

Product 1

HCID 21217692HCID 21217692, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-ethyl-6-methoxycarbonyl-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinoline-4-amine (1.4 g), ethanol (90 ml), KOH (2 g) and water (10 ml) is stirred at room temperature overnight. The reaction mixture is evaporated and the residue is partitioned between CH2Cl2 and water. The aqueous layer is separated, acidified with acetic acid and the solid that forms is collected by filtration and dried. The solid is recrystallized from hot acetic acid (50 ml) to afford 1.0 g of 1-ethyl-6-carboxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine. HOAc, m.p. 240° C.

Workup

  1. customThe reaction mixture is evaporated
  2. customthe residue is partitioned between CH2Cl2 and water
  3. customThe aqueous layer is separated
  4. filtrationthe solid that forms is collected by filtration
  5. customdried
  6. customThe solid is recrystallized from hot acetic acid (50 ml)

Sources & evidence

ORD record
ord-5a4345fa249c4cedb61d24be2c9c892f
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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