Sodium Hydroxide → HCID 10567395, compound

HRID 726701Notes

Reaction equation

HRID 726701 reaction equation
[F:1][C:2]1([F:25])[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]([C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH2:4][CH2:3]1.[OH-].[Na+]>C(O)(=O)C>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]([N:5]2[C:6]3[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=3[C:8](=[O:9])[C:2]([F:25])([F:1])[CH2:3][CH2:4]2)=[O:24])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10545524HCID 10545524, compound

Product 1

HCID 10567395HCID 10567395, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4,4-Difluoro-1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one (940 mg) was dissolved in 20 ml of acetic acid, 3.07 g of stannous chloride was added to the solution at room temperature and then the resulting mixture was heated under reflux for 5 hours. The reaction solution was ice-cooled and adjusted to a basic range with 1N sodium hydroxide. Then, after separating the organic layer, the water layer was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous potassium carbonate and the solvent was evaporated under a reduced pressure. The thus prepared residue was recrystallized from chloroformhexane to obtain 711 mg of 1-(4-aminobenzoyl)-4,4-difluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 5 hours
  3. temperaturecooled
  4. customThen, after separating the organic layer
  5. extractionthe water layer was extracted with ethyl acetate
  6. dry with materialThe resulting organic layer was dried over anhydrous potassium carbonate
  7. customthe solvent was evaporated under a reduced pressure
  8. customThe thus prepared residue was recrystallized from chloroformhexane

Sources & evidence

ORD record
ord-652ded4a9c774e0bafb8ac9254830fb4
Source dataset
uspto-grants-1998_01
Patent number
US05710150

Reaction notes

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