Aluminum(III) Chloride → 6-Hydroxy-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

HRID 1759307Notes

Reaction equation

HRID 1759307 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C[O:6][C:7]1[C:12]2[CH2:13][CH2:14][CH2:15][C:16](=[O:18])[NH:17][C:11]=2[CH:10]=[CH:9][CH:8]=1>CN(C=O)C>[OH:6][C:7]1[C:12]2[CH2:13][CH2:14][CH2:15][C:16](=[O:18])[NH:17][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 99423616-methoxy-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one

Product 1

HCID 99422906-Hydroxy-1,3,4,5-tetrahydro-2H-1-benzazepin-2-oneYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 ml of DMF are added to 65 g of anhydrous aluminum chloride with vigorous stirring, and cooling if necessary. 13.5 g (0.07 mole) of 6-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one are introduced in portions into the resulting melt, and the contents of the flask are then heated to 110°-140° C., left at this temperature for 10 minutes, and thereafter stirred for a further 30 minutes without additional heating. The contents of the flask are then poured into ice water, the sand-colored precipitate formed is filtered off and the filtrate is re-extracted repeatedly with ether. The ether phases are combined, dried and concentrated on a rotary evaporator. The residue is recrystallized from an acetone/cyclohexane/ethyl acetate mixture in the presence of animal charcoal. 6.3 g of 6-hydroxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (51% yield), of melting point 244°-245° C., are obtained.

Workup

  1. temperaturecooling if necessary
  2. temperaturethe contents of the flask are then heated to 110°-140° C.
  3. customthe sand-colored precipitate formed
  4. filtrationis filtered off
  5. extractionthe filtrate is re-extracted repeatedly with ether
  6. customdried
  7. concentrationconcentrated on a rotary evaporator
  8. customThe residue is recrystallized from an acetone/cyclohexane/ethyl acetate mixture in the presence of animal charcoal

Sources & evidence

ORD record
ord-94286c6e98ff45e58953a9b385c2e384
Source dataset
uspto-grants-1982_07
Patent number
US04340595

Reaction notes

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