Trifluoroacetic acid → HCID 66964636, compound

HRID 1630698Notes

Reaction equation

HRID 1630698 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]2[CH:7]=[CH:8][CH2:9][CH2:10][NH:11][C:5]=2[CH:4]=1.FC(F)(F)C(O)=O>C(O)C.[OH-].[Pd+2].[OH-]>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][NH:11][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66965143HCID 66965143, compound

Product 1

HCID 66964636HCID 66964636, compoundYield 169.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of the 8-methoxydihydrobenzazepine (0.45 g, 1.6 mmol) from step F above in ethanol (60 mL) were added trifluoroacetic acid (0.8 mL) and palladium(II) hydroxide (0.15 g, 0.21 mmol). The reaction solution was shaken under hydrogen (35 psi) for 16 hours. The resultant reaction mixture was filtered through a pad of Celite and the filtrate obtained was concentrated in vacuo to give the desired 8-methoxybenzazepine (0.47 g, quantitative), which was used in the next step without purification: ESI MS m/z 282 [M+H]+.

Workup

  1. customThe resultant reaction mixture
  2. filtrationwas filtered through a pad of Celite
  3. customthe filtrate obtained
  4. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-7521de29867744e4be56a146b876f839
Source dataset
uspto-grants-2014_07
Patent number
US08791101B2

Reaction notes

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