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

HRID 1244239Notes

Reaction equation

HRID 1244239 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][CH2:2]1.[N+:12]([O-])([OH:14])=[O:13]>>[N+:12]([C:6]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][NH:1][CH2:2][CH2:3][C:4]=2[CH:5]=1)([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 5765032,3,4,5-tetrahydro-1H-1-benzazepine

Product 1

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

Procedure

1,2,4,5-Tetrahydro-3H-benzazepine (1 g) (See P. Ruggli et al., Helv. Chim. Acta, 18, 1388, [1935]) was added slowly dropwise to stirred fuming nitric acid (25 ml) at −10° C. Stirring was continued at −10° C. 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, 1.4 g. This was suspended in water, cooled to 5° C. and neutralised with 5M sodium hydroxide. The precipitate was collected by filtration, recrystallised from water and dried, affording the title compound D1a as a white solid (0.6 g)

Workup

  1. additionthe reaction mixture was then poured onto ice
  2. filtrationthe precipitate collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-a00c894bb5304009aa78ac0a53c0f2ff
Source dataset
uspto-grants-2006_10
Patent number
US07122538B2

Reaction notes

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