Sodium Carbonate → HCID 119086060, compound

HRID 539959Notes

Reaction equation

HRID 539959 reaction equation
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=O)[CH2:4][CH2:3][CH2:2]1.Cl.[CH3:14][O:15][NH2:16].C([O-])(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:14][O:15]/[N:16]=[C:9]1/[CH2:8][CH2:7][NH:1][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:11][C:10]/1=2

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 2947881,2,3,4-Tetrahydro-benzo(b)azepin-5-oneHCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 119086060HCID 119086060, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,2,3,4-tetrahydro-1-benzazepin-5-one (500 mg, 2.530 mmol), O-methyl hydroxylamine hydrochloride (211 mg, 2.530 mmol), sodium acetate (208 mg, 2.530 mmol) and sodium carbonate (536 mg, 5.060 mmol) in ethanol was refluxed for 3 hours. The resulting mixture was concentrated in vacuo to remove ethanol and to the residue was added water (15 mL). The residue in water was extracted with dichloromethane (15 mL×3). The organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to afford 326 mg of the desired product (yield was 67%).

Workup

  1. temperaturewas refluxed for 3 hours
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. customto remove ethanol
  4. additionto the residue was added water (15 mL)
  5. extractionThe residue in water was extracted with dichloromethane (15 mL×3)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4362013957b946a79274110c85bb1904
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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