Water → HCID 18976807, compound

HRID 1377217Notes

Reaction equation

HRID 1377217 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][C:32]5[CH:37]=[CH:36][C:35]([CH2:38][C:39]6[CH:44]=[CH:43][C:42]([N+:45]([O-])=O)=[CH:41][CH:40]=6)=[CH:34][CH:33]=5)=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.O.[H][H]>O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][C:32]5[CH:37]=[CH:36][C:35]([CH2:38][C:39]6[CH:40]=[CH:41][C:42]([NH2:45])=[CH:43][CH:44]=6)=[CH:34][CH:33]=5)=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)=[CH:15][CH:16]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 962Water2×HCID 22921204HCID 22921204, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18976807HCID 18976807, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a 1-liter three-necked flask equipped with a stirring device and a nitrogen substituting device, 16.4 g of 1,1-bis(4-(4-(4-nitrophenylmethyl)phenylmethyl)phenyl)methane was dissolved in 500 milliliters of tetrahydrofuran, 1.7 g of a Pd-C catalyst (a 5% product, containing 54.8% of water) was added and contacted with hydrogen gas while cooled with water at a normal pressure and then stirred. After absorption of hydrogen was stopped, the catalyst was filtered off and the objective product adhered to a residual layer of the catalyst was washed with chloroform thoroughly and then the filtrate was concentrated. By recrystallizing the concentrate from a chloroform solvent, 11.0 g of a diamino compound according to the invention, that is, 1,1-bis(4-(4-(4-aminophenylmethyl)phenylmethyl)phenyl)methane was obtained as crystals. Melting point was from 192.0° to 193.0° C.

Workup

  1. customIn a 1-liter three-necked flask equipped with a stirring device
  2. additionwas added
  3. customAfter absorption of hydrogen
  4. filtrationthe catalyst was filtered off
  5. washwas washed with chloroform thoroughly
  6. concentrationthe filtrate was concentrated
  7. customBy recrystallizing the
  8. concentrationconcentrate from a chloroform solvent, 11.0 g of a diamino compound

Sources & evidence

ORD record
ord-e498b8ef08764bea9ff88e32bbee046d
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

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