Potassium Acetate → HCID 18378674, compound

HRID 2298818Notes

Reaction equation

HRID 2298818 reaction equation
CC1C=CC(S(O[N:12]=[C:13]2[C:22]3[CH:21]=[N:20][CH:19]=[CH:18][C:17]=3[CH2:16][CH2:15][CH2:14]2)(=O)=O)=CC=1.C([O-])(=[O:25])C.[K+]>C(O)C.O>[NH:12]1[C:13](=[O:25])[CH2:14][CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][N:20]=[CH:21][C:22]1=2

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 54166309HCID 54166309, compound

Product 1

HCID 18378674HCID 18378674, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 8-(4-methylphenylsulfonyl)oxyimino-5,6,7,8-tetrahydroisoquinoline (1.2 g) and potassium acetate (7.45 g) in ethanol (25 ml) and water (30 ml) was heated at 95° C. for 23 hours. The solvent was evaporated at reduced pressure, and the residue was basified with saturated aqueous sodium hydrogencarbonate solution and extracted with chloroform. The dried extract (dried over sodium sulfate) was evaporated at reduced pressure to give crude product. After partial purification by column chromatography (SiO2; 30 g, AcOEt/hexane=2/1, then 5% MeOH—CHCl3), the obtained solid was washed with ether to give 2,3,4,5-tetrahydro-1H-pyrido[3,4-b]azepin-2-one (170 mg).

Workup

  1. customThe solvent was evaporated at reduced pressure
  2. extractionextracted with chloroform
  3. extractionThe dried extract
  4. dry with material(dried over sodium sulfate)
  5. customwas evaporated at reduced pressure
  6. customto give crude product
  7. customAfter partial purification by column chromatography (SiO2
  8. wash30 g, AcOEt/hexane=2/1, then 5% MeOH—CHCl3), the obtained solid was washed with ether

Sources & evidence

ORD record
ord-8fc9e921fc434e1d99a4fd9e30c1d9e0
Source dataset
uspto-grants-2002_12
Patent number
US06495542B1

Reaction notes

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