Nitric Acid → 3-acetyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1668598Notes

Reaction equation

[CH2:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][N:3]([C:12](=[O:14])[CH3:13])[CH2:2]1.[N+:15]([O-])([OH:17])=[O:16]>C(O)(=O)C.S(=O)(=O)(O)O>[N+:15]([C:10]1[CH:9]=[CH:8][C:7]2[CH2:1][CH2:2][N:3]([C:12](=[O:14])[CH3:13])[CH2:4][CH2:5][C:6]=2[CH:11]=1)([O-:17])=[O:16]

Participants

Conditions

Temperature: 0 °C

Procedure

1-(1,2,4,5-Tetrahydrobenzo[d]azepin-3-yl)ethanone (3.8 g) was dissolved in a 2:1 mixture of acetic acid and 96% sulphuric acid (15 ml), then the mixture was cooled to 0° C. and a 3:2 mixture of 65% nitric acid and 96% sulphuric acid (2.5 ml) was added dropwise, while the temperature was maintained below 5° C. The mixture was stirred for additional 30 min, then poured into crushed ice (300 g) and extracted with ethyl acetate. The organic phase was washed with 5% aqueous NaHCO3, dried over Na2SO4 and concentrated to afford a crude material (4.3 g). Filtration through a silica gel pad (DCM/MeOH, 98/2) yielded the title compound as a yellow solid (4.0 g, 85% yield).

Workup

additionwas added dropwise, while the temperature
temperaturewas maintained below 5° C
additionpoured
extractionextracted with ethyl acetate
washThe organic phase was washed with 5% aqueous NaHCO3
dry with materialdried over Na2SO4
concentrationconcentrated
customto afford a crude material (4.3 g)
filtrationFiltration through a silica gel pad (DCM/MeOH, 98/2)

Sources & evidence

ORD record: ord-4ea756ec114e412392a5caa3472b9dab
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989444B2

Reaction notes

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