Acetic Acid → 3-Amino-2,3,4,5-tetrahydro-1H-benzazepin-2-one

HRID 1375150Notes

Reaction equation

HRID 1375150 reaction equation
[NH:1]1[C:7](=[O:8])[C:6](=[N:9]O)[CH2:5][CH2:4][C:3]2[CH:11]=[CH:12][CH:13]=[CH:14][C:2]1=2.C(O)(=O)C.[H][H]>CO.[Pd]>[NH2:9][CH:6]1[C:7](=[O:8])[NH:1][C:2]2[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=2[CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 73866833HCID 73866833, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44344333-Amino-2,3,4,5-tetrahydro-1H-benzazepin-2-oneYield 67.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

5 g (26,3 mmol) of 4,5-dihydro-1H-benzo[b]azepine-2,3-dione 3-oxime is taken in 50 ml of methanol then 6,3 g (105 mmol) acetic acid is added. The reaction mixture is left to stir at 50° C. and 5 bar hydrogen pressure for 21 hours in the presence of 1,1 g Pd catalyst (5% on charcoal, containing 50% water). The reaction mixture is evaporated after filtration and the residue is dissolved in 16,5 ml water. 9,5 ml dichloromethane is added and the pH value is adjusted to pH 12–14 with NaOH (32%). After phase separation the aqueous layer is extracted two times with 5,5 ml dichloromethane each. The organic phases are dried over sodium sulfate and evaporated to give 3,12 g 3-amino-1,3,4,5-tetrahydro-benzo[b]azepin-2-one, yield 67,4%, HPLC 94,5 area %, RT=2.45.

Workup

  1. waitThe reaction mixture is left
  2. customThe reaction mixture is evaporated
  3. filtrationafter filtration
  4. dissolutionthe residue is dissolved in 16,5 ml water
  5. addition9,5 ml dichloromethane is added
  6. customAfter phase separation the aqueous layer
  7. extractionis extracted two times with 5,5 ml dichloromethane each
  8. dry with materialThe organic phases are dried over sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-0b49502f14b744b1a3eb1a5149cbcad6
Source dataset
uspto-grants-2007_01
Patent number
US07166720B2

Reaction notes

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