1-Isobutyl-5-nitro-1,2-dihydro-indazol-3-one → 5-Amino-1-isobutyl-1,2-dihydro-indazol-3-one

HRID 490556Notes

Reaction equation

[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-])=O)=[CH:11][CH:12]=2)[C:7](=[O:17])[NH:6]1)[CH:2]([CH3:4])[CH3:3]>CO.[Pd]>[NH2:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:1][CH:2]([CH3:3])[CH3:4])[NH:6][C:7]2=[O:17]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 1-isobutyl-5-nitro-1,2-dihydro-indazol-3-one (0.9 g) in MeOH (50 mL) was added Pd/C(10%) catalyst (0.3 g) and the reaction mixture was stirred for 1 hour at 40° C. under a hydrogen atmosphere using a balloon. After this time the reaction mixture was filtered through Celite® which was washed with more EtOAc. The combined organic solution was evaporated in vacuo for afford the desired 5-amino-1-isobutyl-1,2-dihydro-indazol-3-one (0.6 g) which was taken into the next reaction without further purification. MS (ESI+): 206.1 ([M+H]+).

Workup

filtrationAfter this time the reaction mixture was filtered through Celite® which
washwas washed with more EtOAc
customThe combined organic solution was evaporated in vacuo

Sources & evidence

ORD record: ord-57d0e1d238f14ec2ba5bc8a0496a8774
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528158B2

Reaction notes

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