HCID 178455723, compound → HCID 178455722, compound

HRID 355487Notes

Reaction equation

HRID 355487 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:28]=[C:29]([N+:31]([O-])=O)[CH:30]=1)[C:7]([O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C@H:20]2[CH2:25][CH2:24][C@H:23]([CH2:26][CH3:27])[CH2:22][CH2:21]2)=[CH:16][CH:15]=1)=[O:8])([O-])=O>C(OCC)(=O)C.[C].[Pd]>[NH2:31][C:29]1[CH:28]=[C:6]([CH:5]=[C:4]([NH2:1])[CH:30]=1)[C:7]([O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C@H:20]2[CH2:25][CH2:24][C@H:23]([CH2:26][CH3:27])[CH2:22][CH2:21]2)=[CH:16][CH:15]=1)=[O:8]

Participants

4

Reactant 1

HCID 178455723HCID 178455723, compound

Product 1

HCID 178455722HCID 178455722, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In 300 ml of ethyl acetate was dissolved 15.0 g (0.033 mol) of [4-(trans-4-ethyl-cyclohexyl)phenoxypropyl] 3,5-dinitrobenzoate, and 1.50 g of 5% palladium-carbon was then added thereto and catalytic reduction was carried out at ordinary temperature under atmospheric pressure. After the completion of the reaction, the catalyst was removed by filtration and the solvent was distilled off under reduced pressure to obtain a crystal. The thus obtained crystal was recrystallized from n-heptane/ethyl acetate twice to obtain 11.1 g (0.028 mol) of [4-(trans-4-ethyl-cyclohexyl)phenoxypropyl] 3,5-diaminobenzoate. The melting point of this compound was in the range of 91.5° to 92.4° C.

Workup

  1. additionwas then added
  2. customAfter the completion of the reaction
  3. customthe catalyst was removed by filtration
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto obtain a crystal
  6. customThe thus obtained crystal was recrystallized from n-heptane/ethyl acetate twice

Sources & evidence

ORD record
ord-961d86c2a697457eab7e55c3641320cf
Source dataset
uspto-grants-1998_11
Patent number
US05830976

Reaction notes

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