Aniline → N-Phenylpyren-1-amine

HRID 480407Notes

Reaction equation

HRID 480407 reaction equation
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[C:18]1([NH2:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.CC(C)([O-])C.[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.[Pd].C1(C)C=CC=CC=1>[C:18]1([NH:24][C:2]2[C:15]3[C:16]4=[C:17]5[C:12](=[CH:13][CH:14]=3)[CH:11]=[CH:10][CH:9]=[C:8]5[CH:7]=[CH:6][C:5]4=[CH:4][CH:3]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 1596271-BromopyreneHCID 23676156Sodium t-butoxide

Product 1

HCID 17809376N-Phenylpyren-1-amineYield 89%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Procedure

1-Bromopyrene (10 mmol), C6H5NH2 (12 mmol), Pd(dba)2 (0.20 mmol), P(t-Bu)3 (0.20-0.30 mmol) and sodium t-butoxide (1.44 g, 15 mmol) were charged in a two-necked flask under a nitrogen atmosphere. Toluene (25 ml) was added and the resulting violet solution was stirred at room temperature for 8 hours. During this period the contents of the flask became a pale yellow fluorescent solution. The reaction was quenched with water (30 ml) and the organic layer was taken into 100 ml diethyl ether, washed with brine solution, and dried over MgSO4. Evaporation of the solvent under vacuum resulted in a yellow solid that was adsorbed in silica gel and purified by column chromatography using dichloromethane/hexane (1:1) as eluant to produce phenyl-pyren-1-yl-amine (89%).

Workup

  1. waitDuring this period the contents of the flask became
  2. customThe reaction was quenched with water (30 ml)
  3. washwashed with brine solution
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent under vacuum
  6. customresulted in a yellow solid
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-d1912462d8b9484e8533dcf149e5658e
Source dataset
uspto-grants-2003_11
Patent number
US06649772B2

Reaction notes

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