4-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butan-1-ol → 4-(4-amino-2-propyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-1-yl)butan-1-ol

HRID 2283852Notes

Reaction equation

HRID 2283852 reaction equation
[NH2:1][C:2]1[C:11]2=[N:12][N:13]([CH2:20][CH2:21][CH3:22])[C:14]([CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1>[OH-].[Na+]>[NH2:1][C:2]1[C:11]2=[N:12][N:13]([CH2:20][CH2:21][CH3:22])[C:14]([CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=[C:10]2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

3

Reactant 1

HCID 577175804-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butan-1-ol

Product 1

HCID 577175984-(4-amino-2-propyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-1-yl)butan-1-olYield 600.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

4-(4-Amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butan-1-ol (prepared as described in Example 593, 0.118 g, 0.396 mmol) was hydrogenated for 1.8 days using the method described in Example 59. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure to yield an oil that was dissolved in 6 M aqueous sodium hydroxide (20 mL). The mixture was stirred for 1 day, then a white solid was isolated by filtration, washed with water, and dried at 70° C. under vacuum to provide 0.719 g of 4-(4-amino-2-propyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-1-yl)butan-1-ol as a white powder, mp 194.0-200.0° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto yield an oil that
  4. customa white solid was isolated by filtration
  5. washwashed with water
  6. customdried at 70° C. under vacuum

Sources & evidence

ORD record
ord-1ad1a45f9dd940718c627615c85abab7
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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