1,1,4,4-Tetramethyl-6-nitro-1,2,3,4-tetrahydronaphthalene → 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine

HRID 1790190Notes

Reaction equation

HRID 1790190 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:10]([CH3:15])([CH3:14])[CH2:9][CH2:8][C:7]([CH3:17])([CH3:16])[C:6]=2[CH:5]=1)([O-])=O.[H][H]>ClCCl.[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][C:11]2[C:10]([CH3:15])([CH3:14])[CH2:9][CH2:8][C:7]([CH3:17])([CH3:16])[C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 139871261,1,4,4-Tetramethyl-6-nitro-1,2,3,4-tetrahydronaphthaleneHCID 178418361HCID 178418361, compound

Product 1

HCID 114697605,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-nitro-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene (79.0 g, 0.339 mol) in dichloromethane as added 1 g of 10% palladium on carbon and the mixture was hydrogenated at 40–50 psi of hydrogen for 20 hrs. The catalyst was removed by filtration and the organic and the aqueous layers were separated. The aqueous layer was made alkaline by addition of 1N NaOH and extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and evaporated to give 2-amino-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene as a red-orange solid which was used in the next step without further purification.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe organic and the aqueous layers were separated
  3. additionby addition of 1N NaOH
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c298b3b7776043f6998b7e42bc24f8c8
Source dataset
uspto-grants-2006_07
Patent number
US07071218B2

Reaction notes

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