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

HRID 1727617Notes

Reaction equation

HRID 1727617 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 stirring 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-37abe9e73e974815a003f2aa39f17a5e
Source dataset
uspto-grants-2009_02
Patent number
US07495103B2

Reaction notes

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