HCID 22413374, compound → HCID 22413368, compound

HRID 1721593Notes

Reaction equation

HRID 1721593 reaction equation
[O:1]1[C:5]2[C:6]([CH:10]3[C:16]4[CH:17]=[CH:18][C:19]([OH:22])=[C:20]([OH:21])[C:15]=4[CH2:14][CH2:13][N:12]([CH3:23])[CH2:11]3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1>C(O)C.C(O)(=O)C>[O:1]1[C:5]2[C:6]([CH:10]3[C:16]4[CH:17]=[CH:18][C:19]([OH:22])=[C:20]([OH:21])[C:15]=4[CH2:14][CH2:13][N:12]([CH3:23])[CH2:11]3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 22413374HCID 22413374, compound

Product 1

HCID 22413368HCID 22413368, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

0.5 g (0.0016 mol) 1-(benzofuran-7-yl)-6,7-dihydroxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine was dissolved in a mixture of 25 ml ethanol and 2 ml acetic acid. 0.2 g catalyst (10% Pd/C) was added and the mixture was submitted to hydrogenation in a Parr apparatus at a pressure of 50 psi. After 24 h the catalyst was filtered off and the solution was concentrated in vacuo. The residue was redissolved in dichloromethane, the solution was washed subsequently with NaHCO3-solution, water and brine. Evaporation in vacuo gave 1-(2,3-dihydrobenzofuran-7-yl)-6,7-dihydroxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine as an offwhite foam.

Workup

  1. filtrationAfter 24 h the catalyst was filtered off
  2. concentrationthe solution was concentrated in vacuo
  3. dissolutionThe residue was redissolved in dichloromethane
  4. washthe solution was washed subsequently with NaHCO3-solution, water and brine
  5. customEvaporation in vacuo

Sources & evidence

ORD record
ord-e33998e8b3ff4e689efc0dc09604e428
Source dataset
uspto-grants-1996_04
Patent number
US05512562

Reaction notes

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