Acetone → HCID 21419384, compound

HRID 441579Notes

Reaction equation

HRID 441579 reaction equation
[CH3:1][C:2]([CH3:4])=O.[BrH:5].[NH2:6][CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:18])[C:13]=2[OH:17])[C:8]1=[O:19].C([O-])(=O)C.[Na+].[H][H]>[Pt](=O)=O.C(O)C>[BrH:5].[OH:19][CH:8]1[C:9]2[C:14](=[C:13]([OH:17])[C:12]([OH:18])=[CH:11][CH:10]=2)[CH2:15][CH2:16][CH:7]1[NH:6][CH:2]([CH3:4])[CH3:1]

Participants

7

Reactant 4

HCID 180AcetoneHCID 517045Sodium AcetateHCID 12353616HCID 12353616, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21419384HCID 21419384, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

In a mixture of 1 volume part of acetone and 10 volume parts of ethanol, there is dissolved 0.100 part of 3,4-dihydro-2-amino-5,6-dihydroxy-1(2H)-naphthalenone hydrobromide and with the addition of 0.0115 part of platinum dioxide and 0.038 part of anhydrous sodium acetate, catalytic reduction is carried out in a current of hydrogen gas. After a substantially stoichiometric amount of hydrogen gas has been absorbed, 0.4 volume part of a 48 % aqueous solution of hydrogen bromide is added. The mixture is filtered and the filtrate is concentrated. A small amount of ethanol is added to the residue and, after the insolubles are removed, the filtrate is concentrated a second time. Finally the residue is recrystallized from acetone. The procedure gives 1,5,6-trihydroxy-2-isopropylamino-1,2,3,4-tetrahydronaphthalene hydrobromide. Melting point: 167° to 169° C.(decomp.)

Workup

  1. customAfter a substantially stoichiometric amount of hydrogen gas has been absorbed
  2. addition0.4 volume part of a 48 % aqueous solution of hydrogen bromide is added
  3. filtrationThe mixture is filtered
  4. concentrationthe filtrate is concentrated
  5. additionA small amount of ethanol is added to the residue
  6. customafter the insolubles are removed
  7. concentrationthe filtrate is concentrated a second time
  8. customFinally the residue is recrystallized from acetone

Sources & evidence

ORD record
ord-06569a6e860d4d40b216867744edd8a5
Source dataset
uspto-grants-1977_08
Patent number
US04041079

Reaction notes

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