HCID 12390936, compound → HCID 12390989, compound

HRID 596256Notes

Reaction equation

HRID 596256 reaction equation
[BrH:1].[CH:2]1([NH:7][CH:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:19])[C:14]=3[OH:18])[C:9]2=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3]1>[Pd].O>[BrH:1].[CH:2]1([NH:7][CH:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:19])[C:14]=3[OH:18])[CH:9]2[OH:20])[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 12390936HCID 12390936, compound

Product 1

HCID 12390989HCID 12390989, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Using 2 parts of 5 % palladium-on-carbon, 2 parts of 2-cyclopentylamino-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. After a stoichiometric amount of hydrogen has been absorbed, the reaction is terminated and the catalyst is filtered off. The filtrate is freeze-dried and the residue is recrystallized from a mixture of ethanol and ethyl acetate. The procedure yields 1.54 parts of 2-cyclopentylamino-1,5,6-trihydroxy-1,2,3,4-tetrahydronaphthalene hydrobromide as colorless crystals melting at 210°-218° C (decomposition).

Workup

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

Sources & evidence

ORD record
ord-a87a8b6607ff45a2b0e98108e721f2e7
Source dataset
uspto-grants-1977_03
Patent number
US04010202

Reaction notes

Loading…