HCID 22404894, compound → HCID 22404907, compound

HRID 440823Notes

Reaction equation

HRID 440823 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([N+:24]([O-])=O)[CH:23]=1)[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)([O-])=O.[H][H]>C(OCC)(=O)C.[Pt]=O>[C:12]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]2[CH:5]=[C:4]([NH2:1])[CH:23]=[C:22]([NH2:24])[CH:21]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 22404894HCID 22404894, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22404907HCID 22404907, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.65 g of 4-(3,5-dinitro-benzyloxy)-biphenyl in 30 ml of ethyl acetate were exhaustively hydrogenated in a hydrogen atmosphere with the addition of 200 mg of platinum oxide. Subsequently, the reaction mixture was filtered over Dicalite and the filtrate was concentrated. The residue was recrystallized from ether/hexane and yielded 5-(biphenyl-4-yloxymethyl)-benzene-1,3-diamine in the form of colourless crystals, MS: m/z 290 ([M]+).

Workup

  1. filtrationSubsequently, the reaction mixture was filtered over Dicalite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was recrystallized from ether/hexane

Sources & evidence

ORD record
ord-9c7ef9486dcd4754a72be1b425386570
Source dataset
uspto-grants-1996_05
Patent number
US05521160

Reaction notes

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