Aluminum(III) Chloride → 3-methyl-4,5-dihydro-1H-benzo[d]azepin-2(3H)-one

HRID 1041771Notes

Reaction equation

HRID 1041771 reaction equation
Cl[CH2:2][C:3]([N:5]([CH3:14])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[Cl-].[Cl-].[Cl-].[Al+3]>>[CH3:14][N:5]1[CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:2][C:3]1=[O:4]

Participants

3

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 125579522-Chloro-N-methyl-N-(2-phenylethyl)acetamide

Product 1

HCID 8521743-methyl-4,5-dihydro-1H-benzo[d]azepin-2(3H)-oneYield 110.5%

Procedure

At 140° C., 2-chloro-N-methyl-N-phenethyl-acetamide (20 g, 94 mmol) and aluminum trichloride (18.9 g, 142 mmol, 1.5 eq.) were heated for 8 hours. The mixture was allowed to cool to ambient temperature and poured over ice. The mixture was extracted with dichlomethane (3×200 mL) and dried with sodium sulfate. The solvent was evaporated to give 3-methyl-1,3,4,5-tetrahydro-benzo[d]azepin-2-one (18.2 g, 100%): 1H NMR (300 MHz, CDCl3) δ 7.1 (m, 4H), 3.92 (s, 2H), 3.71 (t, 2H), 3.15 (t, 2H), 3.03 (s, 3H).

Workup

  1. additionpoured over ice
  2. extractionThe mixture was extracted with dichlomethane (3×200 mL)
  3. dry with materialdried with sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-f30c19bedf1b40adb04d3573c13d8ce5
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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