HCID 12390938, compound → 2-Cyclohexylamino-1,5,6-trihydroxy-1,2,3,4-tetrahydronaphthalene hydrobromide

HRID 596255Notes

Reaction equation

HRID 596255 reaction equation
[BrH:1].[CH:2]1([NH:8][CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:20])[C:15]=3[OH:19])[C:10]2=[O:21])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>[Pd].O>[BrH:1].[CH:2]1([NH:8][CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:20])[C:15]=3[OH:19])[CH:10]2[OH:21])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 12390938HCID 12390938, compound

Product 1

HCID 123909912-Cyclohexylamino-1,5,6-trihydroxy-1,2,3,4-tetrahydronaphthalene hydrobromide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Using 1.91 parts of 5 % palladium-on-carbon, 1.89 parts of 2-cyclohexylamino-5,6-dihydroxy-3,4-dihydro-1(2H)-naphthalenone hydrobromide in 50 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 the filtrate is freeze-dried. The residue is recrystallized from a mixture of ethanol and ethyl acetate, whereby 2-cyclohexylamino-1,5,6-trihydroxy-1,2,3,4-tetrahydronaphthalene hydrobromide is obtained as colorless crystals. Yield 1.38 parts; melting point: 230°-236° C (decomposition).

Workup

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

Sources & evidence

ORD record
ord-f3edbb1fb9be4b6eb049f5b8fe126452
Source dataset
uspto-grants-1977_03
Patent number
US04010202

Reaction notes

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