5-(6-Benzyloxy-3,4-dihydronaphthalen-2-yl)-6-nitrobenzo[1,3]dioxole → 6-(6-Aminobenzo[1,3]dioxole-5-yl)-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950121Notes

Reaction equation

HRID 1950121 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]1[C:27]([N+:28]([O-])=O)=[CH:26][C:22]3[O:23][CH2:24][O:25][C:21]=3[CH:20]=1)[CH2:13][CH2:12]2)C1C=CC=CC=1>C(O)(=O)C.[OH-].[Pd+2].[OH-]>[NH2:28][C:27]1[C:19]([CH:14]2[CH2:13][CH2:12][C:11]3[CH:10]=[C:9]([OH:8])[CH:18]=[CH:17][C:16]=3[CH2:15]2)=[CH:20][C:21]2[O:25][CH2:24][O:23][C:22]=2[CH:26]=1

Participants

4

Reactant 1

HCID 666270645-(6-Benzyloxy-3,4-dihydronaphthalen-2-yl)-6-nitrobenzo[1,3]dioxole

Product 1

HCID 230874786-(6-Aminobenzo[1,3]dioxole-5-yl)-5,6,7,8-tetrahydronaphthalen-2-olYield 40.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 5-(6-benzyloxy-3,4-dihydronaphthalen-2-yl)-6-nitrobenzo[1,3]dioxole (832 mg) in acetic acid (10 ml) was added 20% palladium hydroxide-activated charcoal (200 mg), and the solution was stirred for 13 hours at room temperature under a hydrogen atmosphere at 4 atmospheric pressures. After filtration through celite pad, the solution was concentrated, neutralized with aqueous ammonia, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (240 mg).

Workup

  1. filtrationAfter filtration through celite pad
  2. concentrationthe solution was concentrated
  3. extractionextracted with ethyl acetate
  4. washsequentially washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-98f29125080043858e34c325d214855b
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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