Sodium Chloride → 7-Methyl-8-(trifluoromethyl)-1,2,3,4-tetrahydro-5H-1-benzazepin-5-one

HRID 507028Notes

Reaction equation

HRID 507028 reaction equation
[CH3:1][C:2]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:5]2[N:6](C(OC(C)C)=O)[CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1.[Cl-].[Na+]>O.CS(C)=O>[CH3:1][C:2]1[C:19]([C:20]([F:23])([F:21])[F:22])=[CH:18][C:5]2[NH:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 59432498Propan-2-yl 7-methyl-5-oxo-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1H-1-benzazepine-1-carboxylate

Product 1

HCID 594323957-Methyl-8-(trifluoromethyl)-1,2,3,4-tetrahydro-5H-1-benzazepin-5-oneYield 80%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

Heat a degassed mixture of isopropyl 7-methyl-5-oxo-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (6.68 g, 20.28 mmol) and sodium chloride (37.5 g) in water (7 mL) and dimethyl sulfoxide (180 mL) at reflux under nitrogen for 5 h. Dilute the cooled mixture with water (500 mL) and extract with ethyl acetate (2×300 mL). Wash the combined organic extracts with brine (200 mL), dry over anhydrous sodium sulfate and filter. Remove the solvents under reduced pressure and purify the residue by column chromatography on silica gel, eluting with ethyl acetate/hexanes (1:4), to afford the title compound as a yellow solid (3.94 g, 80%). ESI MS m/z 242 (M−H)−.

Workup

  1. temperatureHeat
  2. temperatureat reflux under nitrogen for 5 h
  3. extractionextract with ethyl acetate (2×300 mL)
  4. washWash the combined organic extracts with brine (200 mL)
  5. dry with materialdry over anhydrous sodium sulfate
  6. filtrationfilter
  7. customRemove the solvents under reduced pressure
  8. custompurify the residue by column chromatography on silica gel
  9. washeluting with ethyl acetate/hexanes (1:4)

Sources & evidence

ORD record
ord-e7dbfbde3af6400fbcf2ccd8d969fa6d
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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