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

HRID 2189673Notes

Reaction equation

HRID 2189673 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-c270e32e976c4bdca4b1df8ef80be5c3
Source dataset
uspto-grants-2012_12
Patent number
US08324242B2

Reaction notes

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