M-Phenylenediamine → N~1~,N~3~-Di(naphthalen-2-yl)benzene-1,3-diamine

HRID 1976519Notes

Reaction equation

HRID 1976519 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.Br[C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1.[CH3:20][C:21]([CH3:24])([O-])[CH3:22].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2].C1(C)C=CC=CC=1>[CH:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[CH:19][C:10]=1[NH:7][C:3]1[CH:4]=[CH:5][CH:6]=[C:1]([NH:8][C:3]2[CH:4]=[CH:5][C:24]3[C:21](=[CH:22][CH:2]=[CH:1][CH:6]=3)[CH:20]=2)[CH:2]=1

Participants

7

Reactant 3

HCID 7935M-PhenylenediamineHCID 113722-BromonaphthaleneHCID 23676156Sodium t-butoxide

Product 1

HCID 235623N~1~,N~3~-Di(naphthalen-2-yl)benzene-1,3-diamineYield 84.4%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst2×HCID 152416121,1`-Bis(diphenylphosphino)ferroceneCatalystHCID 1140TolueneSolvent

Procedure

Into a 100-ml reaction flask were introduced 5.0 g (46.2 mmol) of m-phenylenediamine, 20.1 g (97.1 mmol) of 2-bromonaphthalene, 222 mg of Pd2 (dba)3, i.e., tris(dibenzylideneacetone)dipalladium, 269 mg of 1,1-bis(diphenylphosphino)ferrocene, and 9.5 g (98.9 mmol) of sodium t-butoxide. After the atmosphere in the flask was replaced with nitrogen, 20 ml of toluene was added to the contents. This mixture was reacted at 120° C. overnight. The reaction mixture was cooled to room temperature and the resultant inorganic salt precipitate was filtered off. The filtrate was washed with water (twice), dried (MgSO4), and then concentrated. The resultant crude crystals were recrystallized from toluene to obtain 7.03 g of the target compound.

Workup

  1. customInto a 100-ml reaction flask
  2. additionwas added to the contents
  3. customThis mixture was reacted at 120° C. overnight
  4. filtrationthe resultant inorganic salt precipitate was filtered off
  5. washThe filtrate was washed with water (twice),
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe resultant crude crystals were recrystallized from toluene

Sources & evidence

ORD record
ord-4ac14e764fe74df7bca0ff87e4628508
Source dataset
uspto-grants-2001_05
Patent number
US06228547B1

Reaction notes

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