Trichloroacetic Acid → 2,3,4,5-tetrahydro-1H-2-benzazepin-3-one

HRID 1041763Notes

Reaction equation

HRID 1041763 reaction equation
[CH2:1]1[C:10](=[O:11])[CH2:9][C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.ClC(Cl)(Cl)C(O)=O.[N-:19]=[N+]=[N-].[Na+]>O>[CH2:9]1[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:2][CH2:1][C:10](=[O:11])[NH:19]1

Participants

5

Reactant 3

HCID 6421Trichloroacetic AcidHCID 33557Sodium AzideHCID 682662-Tetralone

Product 1

HCID 28330792,3,4,5-tetrahydro-1H-2-benzazepin-3-oneYield 72.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At 65° C., β-tetralone (5 g, 34.2 mmol) was dissolved in trichloroacetic acid (56 g, 0.34 mol). Sodium azide (3.3 g, 50 mmol, 1.5 eq.) was then added in portions. The mixture was stirred for 9 h and then water (400 mL) was added. The mixture was extracted with dichloromethane (3×200 mL), dried with sodium sulfate, filtered and concentrated in vacuo. The crude mixture was then recrystallized from dichloromethane/hexane to give 1,2,4,5-tetrahydro-benzo[c]azepin-3-one (4 g): 1H NMR (300 MHz, CDCl3) δ 7.2 (m, 4H), 4.37 (d, 1H), 3.1 (m, 2H), 2.8 (m, 2H) and 1,3,4,5-tetrahydro-benzo[d]azepin-2-one (1.5 g): 1H NMR (300 MHz, CDCl3) δ 7.2 (m, 4H), 3.84 (s, 2H), 3.6 (m, 2H), 3.12 (t, 2H).

Workup

  1. extractionThe mixture was extracted with dichloromethane (3×200 mL)
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude mixture was then recrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-bf18b9dfcaec45c28d03b3ff85819dca
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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