Benzylamine → benzyl-[5-(1H-indazol-6-yloxy)-2-nitrophenyl]-amine

HRID 388995

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[N:11][NH:12]2)=[CH:8][CH:7]=1.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH2:21]([NH:28][C:2]1[CH:3]=[C:4]([O:5][C:6]2[CH:14]=[C:13]3[C:9]([CH:10]=[N:11][NH:12]3)=[CH:8][CH:7]=2)[CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A stirred solution of the nitro compound (2 mmol) in DMF (4 mL) was added with benzylamine (4 mmol) and contents were heated at 100° C. for 6 h. The reaction mixture was cooled to RT and the contents were poured onto ice cold water with vigorous stirring. The solid formed was collected by filtration, washed with water, and dried in vacuo. The residue obtained was purified on silica gel column chromatography using hexane/EtOAC as eluent to provide the product, benzyl-[5-(1H-indazol-6-yloxy)-2-nitrophenyl]-amine as a yellow solid.

Workup

temperatureThe reaction mixture was cooled to RT
additionthe contents were poured onto ice cold water with vigorous stirring
customThe solid formed
filtrationwas collected by filtration
washwashed with water
customdried in vacuo
customThe residue obtained
customwas purified on silica gel column chromatography

Sources & evidence

ORD record: ord-76fa6daddde14148af2f74a1786c7678
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377983B2

Linked notes

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