Nitrogen → 8-Nitro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

HRID 1586920Notes

Reaction equation

HRID 1586920 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N-:15]=[N+]=[N-].[Na+].OS(O)(=O)=O.N#N>CC(O)=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][CH2:9][CH2:10][C:11](=[O:14])[NH:15][C:12]=2[CH:13]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 947NitrogenHCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 384457-Nitro-1-tetralone

Product 1

HCID 40932148-Nitro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-oneYield 30.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

7.87 g of 7-nitro-1-tetralone from step A were placed in 55 ml of AcOH. Next, 7.0 g of NaN3 were added and the resulting mixture was heated to 60° C. Then, 10.3 ml of conc. H2SO4 were slowly added dropwise. N2 evolution took place and the temperature rose to 90° C. The reaction mixture was held at this temperature for 1/2 hour, then cooled and poured cautiously into an ice/28% NaOH solution. The mixture was extracted thoroughly with AcOEt, washed with a small amount of water, dried and evaporated. Flash chromatography on SiO2 (hexane/ethyl acetate (1/1→pure ethyl acetate)) yielded 2.58 g of 2,3,4,5-tetrahydro-8-nitro-2-oxo-1H-1-benzazepine as brown crystals of m.p. 224°-226° C. besides regioisomeric lactam and unreacted starting material.

Workup

  1. customrose to 90° C
  2. temperaturecooled
  3. extractionThe mixture was extracted thoroughly with AcOEt
  4. washwashed with a small amount of water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-3e6d6c4236dc4d0f9d2a79ed523ef4f8
Source dataset
uspto-grants-1993_06
Patent number
US05216148

Reaction notes

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