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

Reaktionsgleichung

Reaktionsgleichung von HRID 2295793
[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

Komponenten

5

Edukt 2

HCID 132459914-(4-Chloro-5,6,7,8-tetrahydro-1-naphthoxy)-3,5-dimethyl-1-nitrobenzeneHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 132460354-(4-Chloro-5,6,7,8-tetrahydro-1-naphthoxy)-3,5-dimethylanilineAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e5580e7d8e7c43efb50461886a12b5db
Quelldatensatz
uspto-grants-1984_01
Patentnummer
US04426385

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