Water → 2h-dibenzo[b,f]azepin-2-one

HRID 718083Notes

Reaction equation

HRID 718083 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH2:16]>CC(C)=O>[CH:1]1[C:2](=[O:16])[CH:3]=[CH:4][C:5]2=[N:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH:9]=[CH:10][C:11]=12

Participants

4

Reactant 2

HCID 962WaterHCID 9212Dibenz(b,f)azepine

Product 1

HCID 2764572h-dibenzo[b,f]azepin-2-oneYield 34%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
4 °C

Procedure

To a solution of Na2HPO4 (2.5 g, 9.32 mmol) in water (95 mL) was added (KSO3)2NO (1.8 g, 12.7 mmol). This solution was added to a solution of the (Z)-5H-dibenzo[b,f]azepine (0.5 g, 2.59 mmol) in acetone (50 mL). This reaction mixture was stirred at 4° C. over night. The solid was filtered and the filtrate was evaporated. The residue was dissolved in ether and water. The 2 layers were split. The organic layer and the solid were mixed and evaporated. The crude product was purified by flash chromatography to afford title compound 374 (170 mg, 34%). MS (m/z): 207 (M+H). Step 2: (Z)-5H-dibenzo[b,f]azepin-2-ol (375)

Workup

  1. filtrationThe solid was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in ether
  4. customThe 2 layers were split
  5. additionThe organic layer and the solid were mixed
  6. customevaporated
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-0eb409563a404357b2b4c94e62488098
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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