4-Chloro-5-(4-chloro-5,6,7,8-tetrahydro-1-naphthoxy)-2-nitrotoluene → 5-Chloro-4-(4-chloro-5,6,7,8-tetrahydro-1-naphthoxy)-2-methylaniline

HRID 978477Notes

Reaction equation

HRID 978477 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[C:12]([Cl:19])=[CH:11][CH:10]=2)=[CH:6][C:5]([CH3:20])=[C:4]([N+:21]([O-])=O)[CH:3]=1>C1(C)C=CC=CC=1.[Pt]>[Cl:1][C:2]1[C:7]([O:8][C:9]2[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[C:12]([Cl:19])=[CH:11][CH:10]=2)=[CH:6][C:5]([CH3:20])=[C:4]([CH:3]=1)[NH2:21]

Participants

4

Reactant 1

HCID 132459894-Chloro-5-(4-chloro-5,6,7,8-tetrahydro-1-naphthoxy)-2-nitrotoluene

Product 1

HCID 138271185-Chloro-4-(4-chloro-5,6,7,8-tetrahydro-1-naphthoxy)-2-methylanilineYield 95.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 45.0 g of 4-chloro-5-(4-chloro-5,6,7,8-tetrahydro-1-naphthoxy)-2-nitrotoluene in 1200 ml of toluene was added 4.5 g of 5% platinum on carbon catalyst. This mixture was then changed to a 2 L stirred Parr pressure reactor. The reactor was flushed twice with nitrogen, then twice with hydrogen and then finally filled with hydrogen to a pressure of 250 psig. The internal pressure was maintained between 200 psig and 250 psig while the internal temperature was maintained between 40° and 45° C. during the course of the reaction. When hydrogen uptake ceased, the reaction mixture was removed from the reactor and filtered through celite. Removal of the toluene in vacuo afforded a yellow oil which slowly solidified. Recrystallization from a hexane-ethyl acetate mixture afforded 39.14 g of the desired aniline as white crystals. mp=180° C. NMR (CDCl3): 1.6-1.9 (m, 4H), 2.05 (s, 3H), 2.5-2.7 (m, 4H), 3.47 (broad s, 2H), 6.33 (d, J=8 Hz, 1H), 6.63 (s, 2H), 7.03 (d, J=8 Hz, 1H).

Workup

  1. customThe reactor was flushed twice with nitrogen
  2. additiontwice with hydrogen and then finally filled with hydrogen to a pressure of 250 psig
  3. temperatureThe internal pressure was maintained between 200 psig and 250 psig while the internal temperature
  4. temperaturewas maintained between 40° and 45° C. during the course of the reaction
  5. customthe reaction mixture was removed from the reactor
  6. filtrationfiltered through celite
  7. customRemoval of the toluene in vacuo
  8. customafforded a yellow oil which
  9. customRecrystallization from a hexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-591fdfa155af49718ce033e6a051ae2e
Source dataset
uspto-grants-1987_05
Patent number
US04665097

Reaction notes

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