Nitric Acid → N-(5-nitro-indan-2-yl)-acetamide

Reaction equation

[C:1]([NH:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2].[N+:14]([O-])([OH:16])=[O:15]>>[C:1]([NH:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 944Nitric Acid

HCID 12452137N-(2,3-Dihydro-1H-inden-2-yl)acetamide

Product 1

HCID 14820512N-(5-nitro-indan-2-yl)-acetamide

Procedure

20.5 g of 2-acetylaminoindan is added gradually into 200 ml of fuming nitric acid under cooling. After the reaction, the reaction mixture is poured onto 100 g of ice, and the solvent is evaporated from the chloroform extract, and the residue is recrystallized from isopropyl alcohol to give 18.6 g of 2-acetylamino-5-nitroindan.

Workup

temperatureunder cooling
customAfter the reaction
customthe solvent is evaporated from the chloroform
extractionextract
customthe residue is recrystallized from isopropyl alcohol

Sources & evidence

ORD record: ord-121b83492bf444a3b2d438e6d8c26b8d
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04963587

Reaction notes

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