Ethyl Acetate → HCID 20135078, compound

HRID 580389Notes

Reaction equation

HRID 580389 reaction equation
[I-].[Li+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[NH:13][C:12](=[O:14])[C:11](C(OC)=O)([CH2:15][CH:16]=[CH2:17])[CH:10]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[CH2:9][C:8]=2[CH:30]=1.C(OCC)(=O)C>N1C=CC=CC=1.O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[NH:13][C:12](=[O:14])[CH:11]([CH2:15][CH:16]=[CH2:17])[CH:10]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)[CH2:9][C:8]=2[CH:30]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 66321Lithium iodideHCID 15128681HCID 15128681, compound

Product 1

HCID 20135078HCID 20135078, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 1049PyridineSolvent

Procedure

Lithium iodide (0.90 g; 6.7 mmole) was added to 7-chloro-1,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-3-(2-propenyl)-2H-1-benzazepin-2-one (670 mg; 1.68 mmole) in pyridine (5 ml), three drops of water were added, and the mixture was refluxed with stirring overnight. The solution was dissolved into ethyl acetate and washed with 1N hydrochloric acid (three times). The organic layer was dried (magnesium sulfate) and concentrated. The crude, brownish solid was dissolved into ethyl acetate and suction-filtered through a pad of silica gel (to remove some of the brown color). The silica gel was rinsed several times with ethyl acetate, and the organic solution was concentrated and vacuum dried, leaving 0.52 g of the title compound as an off-white solid.

Workup

  1. additionwere added
  2. temperaturethe mixture was refluxed
  3. washwashed with 1N hydrochloric acid (three times)
  4. dry with materialThe organic layer was dried (magnesium sulfate)
  5. concentrationconcentrated
  6. dissolutionThe crude, brownish solid was dissolved into ethyl acetate
  7. filtrationsuction-filtered through a pad of silica gel (
  8. customto remove some of the brown color)
  9. washThe silica gel was rinsed several times with ethyl acetate
  10. concentrationthe organic solution was concentrated
  11. customvacuum dried

Sources & evidence

ORD record
ord-cc6bc60af9d14e51b25934bc4611099a
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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