4-azido-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one → 4-amino-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one

HRID 253153Notes

Reaction equation

HRID 253153 reaction equation
[N:1]([CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[C:7](=[O:16])[C:6]([CH3:18])([CH3:17])[CH2:5]1)=[N+]=[N-].[H][H]>CCO.[Pd]>[NH2:1][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[C:7](=[O:16])[C:6]([CH3:18])([CH3:17])[CH2:5]1

Participants

5

Reactant 2

HCID 866140234-azido-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 668449584-amino-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-oneYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-azido-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one (2.50 g, 10.2 mmol) in EtOH (100 mL) at RT was added palladium on carbon (1.08 g, 10.2 mmol) in two portions. A hydrogen balloon was affixed to the reaction flask and the head space above the solvent was purged with H2. After 5 hours, the solution was filtered through a plug of celite and concentrated to provide the crude product as an oil. The residue was purified by column chromatography 100% DCM to 50% (10% MeOH/DCM/1% NH4OH) to provide the title compound as a yellow oil (2.04 g, 91% yield). MS m/z: 220.2 (M+1).

Workup

  1. customthe head space above the solvent was purged with H2
  2. filtrationthe solution was filtered through a plug of celite and
  3. concentrationconcentrated
  4. customto provide the crude product as an oil
  5. customThe residue was purified by column chromatography 100% DCM to 50% (10% MeOH/DCM/1% NH4OH)

Sources & evidence

ORD record
ord-75a060ba9f81472db217a3bcacb2c640
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

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