Nitrobenzene → 1,5-bis(Phenyl-p-tolylamino)naphthalene

HRID 992196

Reaction equation

HRID 992196 reaction equation
N[C:2]1[C:11]2[C:6](=[C:7](N)[CH:8]=[CH:9][CH:10]=2)C=CC=1.I[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[N+]([C:29]1C=CC=CC=1)([O-])=O.[C:35]1([NH:41][C:42]2[C:51]3[C:46](=[C:47]([NH:52][C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)[CH:48]=[CH:49][CH:50]=3)[CH:45]=[CH:44][CH:43]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.IC1C=CC(C)=CC=1>[Cu].C1(C)C=CC=CC=1>[C:53]1([N:52]([C:8]2[CH:7]=[CH:6][C:11]([CH3:2])=[CH:10][CH:9]=2)[C:47]2[C:46]3[C:51](=[C:42]([N:41]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:35]4[CH:36]=[CH:37][C:38]([CH3:29])=[CH:39][CH:40]=4)[CH:43]=[CH:44][CH:45]=3)[CH:50]=[CH:49][CH:48]=2)[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1

Participants

9

Reactant 6

HCID 7416Nitrobenzene2×HCID 11430Potassium Carbonate2×HCID 11575IodobenzeneHCID 122074-IodotolueneHCID 167201,5-DiaminonaphthaleneHCID 2299391,5-Bis(phenylamino)naphthalene

Product 1

HCID 184111421,5-bis(Phenyl-p-tolylamino)naphthalene

Reagents, catalysts & solvents 2

HCID 23978CopperCatalyst2×HCID 1140TolueneSolvent2×

Conditions

Temperature
200 °C

Procedure

8 gram (0.05 mol) of 1,5-diamino naphthalene, 22 gram (0.11 mol) of iodobenzene, 17 gram (0.12 mol) of potassium carbonate, 0.4 gram of copper powder and 50 milliliter of nitrobenzene were introduced in a 100 milliliter three-necked flask for stirring at 200° C. for 30 hours. After the reaction, toluene was added, followed by filtration for removal of inorganic compounds. Toluene and nitrobenzene were removed by distillation in a reduced pressure ambient, and the remainder was subjected to separation refinement in a silica gel column using a 1:3 mixture solvent of toluene and ligroin, to prepare 10 gram of 1,5-bis(phenylamino)naphthalene. Thereafter, 6.2 gram (0.02 mol) of 1,5-bis(phenylamino)naphthalene, 11 gram (0.05 mol) of p-iodotoluene, 7 gram (0.05 mol) of potassium carbonate, 0.3 gram of copper powder and 50 milliliter of nitrobenzene were introduced in a 100 milliliter three-necked flask for stirring at 200° C. for 30 hours. After the reaction, toluene was added, followed by filtration for removal of inorganic compounds. Toluene and nitrobenzene were removed by distillation in a reduced pressure ambient, and the remainder was subjected to separation refinement in a silica gel column using a 1:3 mixture solvent of toluene and ligroin, to prepare 7 gram of 1,5-bis(phenyl-p-tolylamino)naphthalene.

Workup

  1. additionwas added
  2. filtrationfollowed by filtration for removal of inorganic compounds
  3. customToluene and nitrobenzene were removed by distillation in a reduced pressure ambient
  4. customthe remainder was subjected to separation refinement in a silica gel column
  5. customto prepare 10 gram of 1,5-bis(phenylamino)naphthalene
  6. stirringfor stirring at 200° C. for 30 hours
  7. additionwas added
  8. filtrationfollowed by filtration for removal of inorganic compounds
  9. customToluene and nitrobenzene were removed by distillation in a reduced pressure ambient
  10. customthe remainder was subjected to separation refinement in a silica gel column
  11. customto prepare 7 gram of 1,5-bis(phenyl-p-tolylamino)naphthalene

Sources & evidence

ORD record
ord-ffdd0ddee9ae40e1a80bf09ab9ee792c
Source dataset
uspto-grants-2002_10
Patent number
US06468675B1

Linked notes

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