Nitrogen → 2H-3-Benzazepin-2-one, 1,3,4,5-tetrahydro-

HRID 1696534Notes

Reaction equation

HRID 1696534 reaction equation
C1C(=O)CC2C(=CC=CC=2)C1.[N-]=[N+]=[N-].[Na+].N#N.[CH2:18]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH2:22][CH2:21][C:20](=[O:29])[NH:19]1>OP(O)(O)=O.O>[CH2:21]1[C:22]2[CH:23]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:24][CH2:18][NH:19][C:20]1=[O:29]

Participants

7

Reactant 4

HCID 947NitrogenHCID 33557Sodium AzideHCID 682662-TetraloneHCID 28330792,3,4,5-tetrahydro-1H-2-benzazepin-3-one

Product 1

HCID 2042322H-3-Benzazepin-2-one, 1,3,4,5-tetrahydro-Yield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1004Phosphoric AcidSolvent

Procedure

beta-Tetralone (34 mmol) was suspended in 300 mL of 85% H3PO4 and treated portion wise with NaN3 (68 mmol) with vigorous stirring over a period of 1 h. During this time the reaction mixture was brought slowly to about 70° C. After stirring for a further 2 h at 70° C., no more N2 evolution was observed. The reaction mixture was cooled to RT, then poured into cold H2O (400 mL) and extracted with CHCl3 (3×). The organic layer was dried (MgSO4), concentrated and the residue was dissolved in EtOAc and the solid was filtered and washed with EtOAc to yield 4,5-dihydro-1H-benzo[d]azepin-2(3H)-one as a white solid (20% yield) along with a varying amount of the other region isomer 1,2,4,5-tetrahydrobenzo[c]azepin-3-one.

Workup

  1. customwas brought slowly to about 70° C
  2. stirringAfter stirring for a further 2 h at 70° C.
  3. extractionextracted with CHCl3 (3×)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. dissolutionthe residue was dissolved in EtOAc
  7. filtrationthe solid was filtered
  8. washwashed with EtOAc

Sources & evidence

ORD record
ord-3c2872b83c0a455cb31e442793e7462b
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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