Ethanol → HCID 21217692, compound

HRID 375886Notes

Reaction equation

HRID 375886 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) was stirred at room temperature overnight. The reaction mixture was evaporated and the residue was partitioned between CH2Cl2 and water. The aqueous layer was separated, acidified with acetic acid and the solid which formed was collected by filtration and dried. The solid was 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 was evaporated
  2. customthe residue was partitioned between CH2Cl2 and water
  3. customThe aqueous layer was separated
  4. customthe solid which formed
  5. filtrationwas collected by filtration
  6. customdried
  7. customThe solid was recrystallized from hot acetic acid (50 mL)

Sources & evidence

ORD record
ord-f159589771ac41e8a101be7ab333f9fa
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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