tetrakis(4-nitrophenyl)methane → TETRAKIS(4-AMINOPHENYL)METHANE

HRID 1883510Notes

Reaction equation

HRID 1883510 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:29]2[CH:34]=[CH:33][C:32]([N+:35]([O-])=O)=[CH:31][CH:30]=2)([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=2)[C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].O1CCCC1>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)([C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)[C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 10185371tetrakis(4-nitrophenyl)methaneHCID 178418361HCID 178418361, compound

Product 1

HCID 11825069TETRAKIS(4-AMINOPHENYL)METHANE

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a Parr reactor, tetrakis(4-nitrophenyl)methane (17.0 grams, 34.0 mmol; prepared as described in Example B) and palladium, weight percent on activated carbon (2.15 grams, 2.00 mmol; obtained from Aldrich Chemical Co., Milwaukee, Wis.) were added to tetrahydrofuran (450 milliliters). The reactor was closed, and the mixture was stirred under 200 pounds per square inch (13.6 atmospheres) of hydrogen pressure for 72 hours at room temperature. The mixture was then filtered through CELITE, solvent was removed from the filtrate by evaporation under reduced pressure, and the resulting white solid was triturated in chloroform. The solid was then recovered by filtration, washed with chloroform again, and dried under reduced pressure at room temperature to give the targeted tetrakis(4-aminophenyl)methane as a white powder in a quantitative yield (12.9 grams).

Workup

  1. customThe reactor was closed
  2. filtrationThe mixture was then filtered through CELITE, solvent
  3. customwas removed from the filtrate by evaporation under reduced pressure
  4. customthe resulting white solid was triturated in chloroform
  5. filtrationThe solid was then recovered by filtration
  6. washwashed with chloroform again
  7. customdried under reduced pressure at room temperature

Sources & evidence

ORD record
ord-84c2248416344a95a54a7ce1870f8bae
Source dataset
uspto-grants-2004_07
Patent number
US06761758B2

Reaction notes

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