Sulfuric Acid → 1,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

HRID 1456629Notes

Reaction equation

HRID 1456629 reaction equation
[N-:1]=[N+]=[N-].[Na+].[CH2:5]1[CH2:15][C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1.S(=O)(=O)(O)O>C(Cl)(Cl)Cl>[NH:1]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5][CH2:15][C:13]1=[O:14]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 107241-TetraloneHCID 33557Sodium Azide

Product 1

HCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-oneYield 47.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred suspension of 13.4 g (207 mmol) of sodium azide and 25.0 ml (188 mmol) of α-tetralone in 150 mL of chloroform, was added 50.0 mL of concentrated sulfuric acid, dropwise over 1 h. After 30 min., the chloroform phase was decanted and the acidic phase poured into 1 L of water. The precipitated solid was collected on a filter, washed with water, and recrystallized from 1 L of boiling water. The product was collected and dried under vacuum to yield 14.3 g (47%) of tan needles. 1H NMR (300 MHz, CDCl3) d 8.63 (1H, bs), 7.24 (2H, m), 7.13 (1H, m), 7.03 (1H, d, J=8 Hz), 2.82 (2H, t, J=6 Hz), 2.38 (2H, t, J=6 Hz), 2.24 (2H, m).

Workup

  1. waitAfter 30 min.
  2. customthe chloroform phase was decanted
  3. additionthe acidic phase poured into 1 L of water
  4. customThe precipitated solid was collected on a filter
  5. washwashed with water
  6. customrecrystallized from 1 L of boiling water
  7. customThe product was collected
  8. customdried under vacuum

Sources & evidence

ORD record
ord-6e4009d1d22b4e2bb1163b10d6af7515
Source dataset
uspto-grants-1998_12
Patent number
US05843941

Reaction notes

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