Ammonium Hydroxide → HCID 68443954, compound

HRID 1163396Notes

Reaction equation

Cl[C:2]1[CH:19]=[C:18]([F:20])[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[N:12][NH:13]2)=[CH:9][CH:8]=1)=[O:5].[NH4+:24].[OH-]>O1CCOCC1>[NH2:24][C:2]1[CH:19]=[C:18]([F:20])[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[N:12][NH:13]2)=[CH:9][CH:8]=1)=[O:5]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-chloro-4-fluoro-N-(1H-indazol-6-yl)-5-nitrobenzamide (3 mmol) in dioxane (6 mL) was added concentrated aqueous NH4OH (3 mL). The resulting mixture was heated at 60° C. for 2-3 h. The completed reaction afforded the product, 2-amino-4-fluoro-N-(1H-indazol-6-yl)-5-nitrobenzamide. To the crude reaction mixture was added diethylamine (45 mmol). The mixture then heated at 60° C. for 6 h. After the reaction was complete, the volatiles were removed in vacuo, and the residue was suspended in cold water. The solid was collected by filtration, washed with water, and dried in vacuo to provide 4-amino-2-diethylamino-N-(1H-indazol-6-yl)-5-nitrobenzamide.

Workup

customThe completed reaction

Sources & evidence

ORD record: ord-7b6f116f263c4b1aa3790e9f4747cf38
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820821B2

Reaction notes

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