Nitric Acid → 5,5-dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine

HRID 888096Notes

Reaction equation

HRID 888096 reaction equation
OS(O)(=O)=O.[CH3:6][C:7]1([CH3:18])[CH2:13][CH2:12][CH2:11][NH:10][C:9]2[CH:14]=[CH:15][CH:16]=[CH:17][C:8]1=2.[N+:19]([O-])([OH:21])=[O:20]>>[CH3:6][C:7]1([CH3:18])[CH2:13][CH2:12][CH2:11][NH:10][C:9]2[CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:17][C:8]1=2

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 574702555,5-dimethyl-2,3,4,5-tetrahydro-1H-1-benzazepine

Product 1

HCID 574702565,5-dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine

Procedure

H2SO4 (2.5 ml) was cooled in a brine/ice bath. 5,5-Dimethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine (1.1 g, 6.3 mmol) was added drop wise. The resulting slurry was stirred for 30 min. HNO3 (0.26 ml, 6.3 mmol) and more H2SO4 (1.5 ml) were added slowly. The reaction was stirred at 0-15° C. for 2 h, poured into ice water, extracted with EtOAc, washed with brine, dried (MgSO4), filtered and concentrated to give 5,5-Dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine.

Workup

  1. stirringThe reaction was stirred at 0-15° C. for 2 h
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b3b23ab0ea5c4f9eb01dbb84b3ad6be0
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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