HCID 12353626, compound → HCID 21419384, compound

HRID 441578Notes

Reaction equation

HRID 441578 reaction equation
[H][H].[BrH:3].[CH:4]([NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:19])[C:14]=2[OH:18])[C:9]1=[O:20])([CH3:6])[CH3:5]>O.[Pd]>[BrH:3].[OH:20][CH:9]1[C:10]2[C:15](=[C:14]([OH:18])[C:13]([OH:19])=[CH:12][CH:11]=2)[CH2:16][CH2:17][CH:8]1[NH:7][CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 12353626HCID 12353626, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21419384HCID 21419384, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

In 10 volume parts of water is dissolved 0.180 part of 3,4-dihydro-2-isopropylamino-5,6-dihydroxy-1(2H)-naphthalenone hydrobromide and with the addition of 0.2 part of 5 % palladium-on-carbon, catalytic reduction is carried out in a current of hydrogen gas. The absorption of hydrogen ceases when 9 volume parts of hydrogen has been absorbed. The catalyst is filtered off and the filtrate is freeze-dried. Finally, the residue is recrystallized from ethanol-ethyl ether. The procedure gives colorless prisms of 1,5,6-trihydroxy-2-isopropylamino-1,2,3,4-tetrahydronaphthalene hydrobromide. Melting point: 169° C.(decomp.)

Workup

  1. customThe absorption of hydrogen ceases when 9 volume parts of hydrogen
  2. customhas been absorbed
  3. filtrationThe catalyst is filtered off
  4. customthe filtrate is freeze-dried
  5. customFinally, the residue is recrystallized from ethanol-ethyl ether

Sources & evidence

ORD record
ord-ed9585d7eada4fe5bda7aa00a11b0245
Source dataset
uspto-grants-1977_08
Patent number
US04041079

Reaction notes

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