HCID 20316894, compound → HCID 20316906, compound

HRID 596259Notes

Reaction equation

HRID 596259 reaction equation
[BrH:1].[CH:2]1([NH:6][CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([OH:18])[C:13]=3[OH:17])[C:8]2=[O:19])[CH2:5][CH2:4][CH2:3]1>[Pd].O>[BrH:1].[CH:2]1([NH:6][CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([OH:18])[C:13]=3[OH:17])[CH:8]2[OH:19])[CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 20316894HCID 20316894, compound

Product 1

HCID 20316906HCID 20316906, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

In the presence of 1.53 parts of 5 % palladium-on-carbon, 1.5 parts of 2-cyclobutylamino-5,6-dihydroxy-3,4-dihydro-1(2H)-naphthalenone hydrobromide in 200 volume parts of water is subjected to catalytic reduction at ordinary temperature and pressure. When a stoichiometric amount of hydrogen has been absorbed, the reaction mixture is filtered to remove the catalyst and filtrate is freeze-dried. The residue is recrystallized from a mixture of water, ethanol and ethyl ether, whereby 2-cyclobutylamino-1,5,6-trihydroxy-1,2,3,4-tetrahydronaphthalene hydrobromide is obtained as colorless crystals. Yield 0.65 part; melting point: 190°-200° C (decomposition).

Workup

  1. customWhen a stoichiometric amount of hydrogen has been absorbed
  2. filtrationthe reaction mixture is filtered
  3. customto remove the catalyst and filtrate
  4. customis freeze-dried
  5. customThe residue is recrystallized from a mixture of water, ethanol and ethyl ether

Sources & evidence

ORD record
ord-a355a422a6c9424189621424fc0c931e
Source dataset
uspto-grants-1977_03
Patent number
US04010202

Reaction notes

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