7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-nitroisoquinolin-1(2H)-one → 5-amino-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one

HRID 577599Notes

Reaction equation

HRID 577599 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([CH:11]=[CH:12][NH:13][C:14]3=[O:17])=[C:9]([N+:18]([O-:20])=[O:19])[CH:8]=2)=[C:5]([CH3:21])[N:4]=[N:3]1>[Ni].C(O)(C)C>[CH3:1][N:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([CH:11]=[CH:12][NH:13][C:14]3=[O:17])=[C:9]([N+:18]([O-:20])=[O:19])[CH:8]=2)=[C:5]([CH3:21])[N:4]=[N:3]1.[NH2:18][C:9]1[CH:8]=[C:7]([C:6]2[N:2]([CH3:1])[N:3]=[N:4][C:5]=2[CH3:21])[CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][NH:13][C:14]2=[O:17]

Participants

5

Reactant 1

HCID 867238257-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-nitroisoquinolin-1(2H)-one

Product 2

HCID 867238257-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-nitroisoquinolin-1(2H)-oneHCID 867238265-amino-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-oneYield 26%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-nitroisoquinolin-1(2H)-one (293c, 1.0 g, 3.5 mmol) and Raney Nickel (6 g) in isopropanol (60 mL) in a sealed tube was heated at 110-120° C. for three days. Sixteen 1 g batches (16 g 293c total) were prepared by this method, and then combined for purification. The combined solutions were cooled to room temperature and filtered. The filtrate was concentrated under vacuum to ˜30 mL, causing a precipitate to form. The precipitate was collected by filtration to give 5-amino-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one (293d, 4.0 g, 26% yield) as a white solid. The Raney nickel-containing first filter cake was dissolved in methanol/dichloromethane (1:1, 400 mL×4), stirred for 30 minutes, filtered, and the filtrate concentrated under vacuum to give a second batch of 5-amino-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one (293d, 8.0 g, 54% yield) as a grey solid.

Workup

  1. customcombined for purification
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under vacuum to ˜30 mL
  4. customto form
  5. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-cec9541b7e824b9784f3afd40ec18275
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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