1,3-Bis(4-benzoylphenoxy)propane dioxime → 1,3-Bis[4-(alpha-aminobenzyl)phenoxy]propane

HRID 66182Notes

Reaction equation

HRID 66182 reaction equation
[C:1](=[N:34]O)([C:8]1[CH:33]=[CH:32][C:11]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23](=[N:30]O)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.N.[Ni]>[NH2:30][CH:23]([C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][CH2:14][CH2:13][O:12][C:11]2[CH:10]=[CH:9][C:8]([CH:1]([NH2:34])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:33][CH:32]=2)=[CH:18][CH:19]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 2

HCID 867333991,3-Bis(4-benzoylphenoxy)propane dioximeHCID 178418361HCID 178418361, compound

Product 1

HCID 203406961,3-Bis[4-(alpha-aminobenzyl)phenoxy]propane

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

The dioxime from Step 2 (20 g) is dissolved in ethyl alcohol saturated with ammonia gas (220 ml) and Raney nickel W-6 (2 g) added. The mixture is subjected to 500 psi hydrogen pressure and heated at 90° for four hours. The catalyst is removed by filtration and the solvent is removed by distillation to yield 15.5 g (83% of theory) of pale yellow crystals mp 118°-9°.

Workup

  1. addition(2 g) added
  2. temperatureheated at 90° for four hours
  3. customThe catalyst is removed by filtration
  4. customthe solvent is removed by distillation

Sources & evidence

ORD record
ord-8db0af6177b8479294b00d8ad468775e
Source dataset
uspto-grants-1978_12
Patent number
US04130664

Reaction notes

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