Nitric Acid → 7-Nitro-2,3,4,5-tetrahydro-1H-benzo[D]azepine

HRID 329367Notes

Reaction equation

HRID 329367 reaction equation
[CH2:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][NH:3][CH2:2]1.[N+:12]([O-])([OH:14])=[O:13]>>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]2[CH2:5][CH2:4][NH:3][CH2:2][CH2:1][C:7]=2[CH:8]=1)([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 14002432,3,4,5-Tetrahydro-1H-benzo(d)azepine

Product 1

HCID 113100427-Nitro-2,3,4,5-tetrahydro-1H-benzo[D]azepine

Procedure

1,2,4,5-Tetrahydro-3H-3-benzazepine (1 g) (see P. Ruggli et al., Helv. Chem. Acta, 18, 1388 [1935]) was added slowly, dropwise to stirred fuming nitric acid (25 ml. density 1.5 gm/ml) cooled to -10°. Stirring was continued at -10° for 1 hour, and the reaction mixture was then poured onto ice, the precipitate collected by filtration and dried to give the title compound as the nitrate salt, yield 1.4 g. A sample was recrystallised from water, m.p. 203°-204°.

Workup

  1. temperaturecooled to -10°
  2. additionthe reaction mixture was then poured onto ice
  3. filtrationthe precipitate collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-27dbf9b3655445fb8320e416742d1d64
Source dataset
uspto-grants-1990_01
Patent number
US04891372

Reaction notes

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