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

HRID 1688105Notes

Reaction equation

HRID 1688105 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-b1eb978e1d5c4047b434083efdddbf49
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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