Sulfuric Acid → 6-Hydroxy-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

HRID 1759308Notes

Reaction equation

HRID 1759308 reaction equation
C[O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH2:11][C:12](=[O:14])[NH:13][C:7]=2[CH:6]=[CH:5][CH:4]=1.[Cl-].[NH+]1C=CC=CC=1.OS(O)(=O)=O>O>[OH:2][C:3]1[C:8]2[CH2:9][CH2:10][CH2:11][C:12](=[O:14])[NH:13][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 69401Einecs 211-027-4HCID 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 45.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.8 g (0.02 mole) of 6-methoxy-2,3,4,5-tetra-hydro-1H-1-benzazepin-2-one and 10 g of pyridinium chloride are heated for 2 hours at 200°-220° C. The melt is cooled and poured into water, and the mixture is acidified with 2 N H2SO4 and extracted repeatedly with ether. The combined organic phases are dried and concentrated and the residue is recrystallized from an acetone/cyclohexane/ethyl acetate mixture in the presence of animal charcoal. 1.6 g of 6-hydroxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one, of melting point 243°-244° C., are obtained. This material is identical with the product obtained under Ia.

Workup

  1. temperatureThe melt is cooled
  2. extractionextracted repeatedly with ether
  3. customThe combined organic phases are dried
  4. concentrationconcentrated
  5. customthe residue is recrystallized from an acetone/cyclohexane/ethyl acetate mixture in the presence of animal charcoal

Sources & evidence

ORD record
ord-c6f6fa0cc0df4f75b1e21cf4e0774a0c
Source dataset
uspto-grants-1982_07
Patent number
US04340595

Reaction notes

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