Nitric Acid → 7-nitro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

HRID 518835

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

2 g of 1,3,4,5-tetrahydro-2H-1-benzazepin-2-one are added to a solution of 25 ml of nitric acid at 70% in water and of 35 ml of sulfuric acid cooled to 0° C. The reaction medium is stirred for 15 minutes at 0° C. and then poured into water (250 ml) and extracted with ethyl acetate. The organic phase is washed with a saturated aqueous sodium bicarbonate solution and with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is taken up with diisopropyl ether and the insoluble material is filtered off and dried under vacuum, so as to give 1.04 g of 7-nitro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in the form of a beige solid.

Workup

extractionextracted with ethyl acetate
washThe organic phase is washed with a saturated aqueous sodium bicarbonate solution and with water
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
filtrationthe insoluble material is filtered off
customdried under vacuum

Sources & evidence

ORD record: ord-a220b8ec54d947ea9832a6d3eb76f824
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115140B2

Linked notes

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