4-(4-Chloro-5,6,7,8-tetrahydro-1-naphthoxy)-3,5-dimethyl-1-nitrobenzene → 4-(4-Chloro-5,6,7,8-tetrahydro-1-naphthoxy)-3,5-dimethylaniline

HRID 2295793

Reaction equation

HRID 2295793 reaction equation
[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([O:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([N+:20]([O-])=O)=[CH:15][C:14]=2[CH3:23])=[CH:4][CH:3]=1.[H][H]>C1(C)C=CC=CC=1.[Pt]>[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([O:12][C:13]2[C:14]([CH3:23])=[CH:15][C:16]([NH2:20])=[CH:17][C:18]=2[CH3:19])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 132459914-(4-Chloro-5,6,7,8-tetrahydro-1-naphthoxy)-3,5-dimethyl-1-nitrobenzeneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 132460354-(4-Chloro-5,6,7,8-tetrahydro-1-naphthoxy)-3,5-dimethylanilineYield 99.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

A 1 L rocking Parr hydrogenator was charged with a solution containing 19.11 g of 4-(4-chloro-5,6,7,8-tetrahydro-1-naphthoxy)-3,5-dimethyl-1-nitrobenzene in 600 mL of toluene. To this was then added 1.0 g of 5% platinum on carbon. This was then placed under an atmosphere of hydrogen at 100 psi. The internal pressure was maintained between 80 and 100 psi while hydrogen uptake continued. When the hydrogen uptake ceased, the contents of the hydrogenator were removed and the vessel washed with toluene. The washings were combined with the reaction mixture. This was then filtered through celite. Removal of the solvents afforded 17.30 g of pale yellow solid. mp 126°-135° C. NMR(CDCl3): δ1.6-1.8 (m, 4H), 2.0 (S, 6H), 2.6-2.9 (m, 4H), 3.45 (S, 2H), 6.13 (d, J=9 Hz, 1H), 6.37 (S, 2H), 6.93 (d, J= 9 Hz, 1H).

Workup

  1. additionwas charged with a solution
  2. customthe contents of the hydrogenator were removed
  3. washthe vessel washed with toluene
  4. filtrationThis was then filtered through celite
  5. customRemoval of the solvents

Sources & evidence

ORD record
ord-e5580e7d8e7c43efb50461886a12b5db
Source dataset
uspto-grants-1984_01
Patent number
US04426385

Linked notes

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