Sulfuric Acid → 1,3,4,5-Tetrahydro-3-(methoxycarbonyl)-4-(methoxyphenyl)-3-(2-propenyl)-7-(trifluoromethyl)-2H-1-benzazepin-2-one

HRID 580399Notes

Reaction equation

HRID 580399 reaction equation
S(=O)(=O)(O)O.[Br-].[Li+].[CH3:8][O:9][C:10]([C:12]1([CH2:39][CH:40]=[CH2:41])[CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[CH2:17][C:16]2[CH:27]=[C:28]([C:31]([F:34])([F:33])[F:32])[CH:29]=[CH:30][C:15]=2[N:14](COC)[C:13]1=[O:38])=[O:11].C(=O)(O)[O-].[Na+]>CO>[CH3:8][O:9][C:10]([C:12]1([CH2:39][CH:40]=[CH2:41])[CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[CH2:17][C:16]2[CH:27]=[C:28]([C:31]([F:34])([F:32])[F:33])[CH:29]=[CH:30][C:15]=2[NH:14][C:13]1=[O:38])=[O:11]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 82050Lithium BromideHCID 516892Sodium BicarbonateHCID 201350941,3,4,5-Tetrahydro-3-(methoxycarbonyl)-1-(methoxymethyl)-4-(methoxyphenyl)-3-(2-propenyl)-7-(trifluoromethyl)-2H-1-benzazepin-2-one

Product 1

HCID 201351131,3,4,5-Tetrahydro-3-(methoxycarbonyl)-4-(methoxyphenyl)-3-(2-propenyl)-7-(trifluoromethyl)-2H-1-benzazepin-2-oneYield 104.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated sulfuric acid (8 ml) and anhydrous lithium bromide (720 mg; 8 mmole) were added to a suspension of 1,3,4,5-tetrahydro-3-(methoxycarbonyl)-1-(methoxymethyl)-4-(methoxyphenyl)-3-(2-propenyl)-7-(trifluoromethyl)-2H-1-benzazepin-2-one (905 mg; 1.9 mmole) in methanol (40 ml) with stirring. The reaction mixture was heated under reflux (bath temperature=80°-85° C.) for nine hours, and then allowed to stand overnight at room temperature. The acid was carefully neutralized by the addition of saturated sodium bicarbonate solution and extracted with ethyl acetate (three times). The combined organic layers were dried (magnesium sulfate) and concentrated yielding 858 mg of the title compound as a solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux (bath temperature=80°-85° C.) for nine hours
  3. extractionextracted with ethyl acetate (three times)
  4. dry with materialThe combined organic layers were dried (magnesium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-90e0864c8e2f4f38882712c538f62820
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

Loading…