Ammonia → 8-Nitro-2,3,4,5-tetrahydro-1H-1-benzazepine

HRID 1915386Notes

Reaction equation

HRID 1915386 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.[N+:12]([O-])([O-:14])=[O:13].[K+].N>OS(O)(=O)=O>[N+:12]([C:10]1[CH:9]=[CH:8][C:3]2[CH2:4][CH2:5][CH2:6][CH2:7][NH:1][C:2]=2[CH:11]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24434Potassium NitrateHCID 5765032,3,4,5-tetrahydro-1H-1-benzazepine

Product 1

HCID 468640718-Nitro-2,3,4,5-tetrahydro-1H-1-benzazepineYield 52%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

At −10° C., 2,3,4,5-tetrahydro-1H-benzo[b]azepine (1.9 g, 13 mmol) was added dropwise to a solution of KNO3 (3 g, 30 mmol) in H2SO4 (50 mL). The mixture was stirred for 40 min, poured over crushed ice, basified with aq. ammonia to pH 13, and extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4 and concentrated to give 8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine as a black solid (1.3 g, 51%), which was used without further purification.

Workup

  1. additionpoured
  2. customover crushed ice
  3. extractionextracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-21d18a920d5743939263dab1f8eb3128
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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