Ammonia → HCID 57717544, compound

HRID 2283932Notes

Reaction equation

HRID 2283932 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[C:14](=[N:20][N:21]([CH2:23][CH3:24])[CH:22]=3)[C:15](Cl)=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:25]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[C:14](=[N:20][N:21]([CH2:23][CH3:24])[CH:22]=3)[C:15]([NH2:25])=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86604927HCID 86604927, compound

Product 1

HCID 57717544HCID 57717544, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 7-benzyloxy-4-chloro-2-ethyl-2H-pyrazolo[3,4-c]quinoline (1.20 g, 3.55 mmol) and 7 N ammonia in methanol (25 mL) was heated in a pressure vessel at 150° C. for 24 hours. The reaction mixture was concentrated under reduced pressure, purified via column chromatography on silica gel (eluting with 0-35% CMA/chloroform), concentrated under reduced pressure, and crystallized from acetonitrile to yield 0.93 g of 7-(benzyloxy)-2-ethyl-2H-pyrazolo[3,4-c]quinolin-4-amine as a tan solid, mp 229-230° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified via column chromatography on silica gel (eluting with 0-35% CMA/chloroform)
  3. concentrationconcentrated under reduced pressure
  4. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-673877231f3844869dd76b7cd27b56d1
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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