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

HRID 401380Notes

Reaction equation

HRID 401380 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[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.C([O-])(O)=O.[Na+]>OS(O)(=O)=O>[CH3:6][C:7]1([CH3:18])[CH2:13][CH2:12][CH2:11][NH:10][C:9]2[CH:14]=[C:15]([N+:1]([O-:4])=[O:2])[CH:16]=[CH:17][C:8]1=2

Participants

5

Reactant 3

HCID 24434Potassium NitrateHCID 516892Sodium BicarbonateHCID 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]azepineYield 86.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

At 0° C., KNO3 (0.76 g, 7.54 mmol) was added portionwise to a solution of 5,5-dimethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine (1.1 g, 6.28 mmol) in H2SO4 (15 mL). After stifling 15 min at this temperature, the mixture was poured into ice water, basified with sat. NaHCO3 to pH 8 and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give crude 5,5-dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine (1.2 g), which was used directly in the next step without further purification.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3032f45f7d6949cc91f4fff22ba8e27f
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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