Ethanol → 5-(Hydroxymethyl)-2-[(propan-2-yl)amino]-1,2,3,4-tetrahydronaphthalene-1,6-diol

HRID 259014Notes

Reaction equation

HRID 259014 reaction equation
C(O)C.Cl.[OH:5][C:6]1[C:7]([CH2:21][OH:22])=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH:11]([NH:17][CH:18]([CH3:20])[CH3:19])[CH2:10][CH2:9]2.[H][H]>[Pd].C(N(CC)CC)C>[OH:16][CH:12]1[C:13]2[C:8](=[C:7]([CH2:21][OH:22])[C:6]([OH:5])=[CH:15][CH:14]=2)[CH2:9][CH2:10][CH:11]1[NH:17][CH:18]([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 702EthanolHCID 21425580HCID 21425580, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 477285-(Hydroxymethyl)-2-[(propan-2-yl)amino]-1,2,3,4-tetrahydronaphthalene-1,6-diol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

In a mixture of 20 ml. ethanol and 2 ml. of triethylamine is dissolved 200 mg. of 6-hydroxy-5-hydroxymethyl-2-isopropylamino-3,4-dihydro-1(2H)-naphthalenone hydrochloride and, with the addition of 50 mg. of 5 % palladium-on-carbon, the solution is agitated in a current of hydrogen for 15 hours. The catalyst is filtered off and the filtrate is concentrated under reduced pressure. The resiude is dissolved in tetrahydrofuran. The insolubles are filtered off and the filtrate is concentrated under reduced pressure. The residue is recrystallized from ethanol-ethyl acetate. The procedure yields colorless crystals of 1,6-dihydroxy-5-hydroxymethyl-2-isopropylamino-1,2,3,4-tetrahydronaphthalene which is identical with the product according to the procedure of Example 71. Yield 108 mg.

Workup

  1. additionIn a mixture of 20 ml
  2. filtrationThe catalyst is filtered off
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. dissolutionThe resiude is dissolved in tetrahydrofuran
  5. filtrationThe insolubles are filtered off
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customThe residue is recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-1a1065f485364b1a8292ed67c8f3a25e
Source dataset
uspto-grants-1977_07
Patent number
US04035512

Reaction notes

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