HCID 13772931, compound → HCID 13772932, compound

HRID 980569Notes

Reaction equation

HRID 980569 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:23]([O-])=O)[CH:5]=[C:6]([Cl:22])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>[Pt].C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Cl:22])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[NH2:23]

Participants

4

Reactant 1

HCID 13772931HCID 13772931, compound

Product 1

HCID 13772932HCID 13772932, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

A 500 milliliter rocking Parr hydrogenator was charged with a solution of 12 grams (0.032 moles) of 3,5-dichloro-4-(2-phenylphenylmethoxy) nitrobenzene prepared in Part A and 100 milliliters of toluene. To this solution was added 1.0 gram of a catalyst of 5% platinum on carbon and the reactor was sealed. The reactor was purged twice with nitrogen and then twice with hydrogen. Hydrogen was then introduced to a pressure of 26 psi and this pressure was maintained until the hydrogen up-take ceased, i.e., about 20 minutes. The material was removed from the reactor, filtered through celite and concentrated (toluene removed under vacuum) to give an oil. Crystallization from a hexane-ethyl acetate mixture (5:2 volume ratio) afforded 9.09 grams of an ivory powder having a melting point of 67.0° C.-69.0° C.

Workup

  1. customthe reactor was sealed
  2. customThe reactor was purged twice with nitrogen
  3. additionHydrogen was then introduced to a pressure of 26 psi
  4. temperaturethis pressure was maintained until the hydrogen
  5. customi.e., about 20 minutes
  6. customThe material was removed from the reactor
  7. filtrationfiltered through celite and
  8. concentrationconcentrated
  9. custom(toluene removed under vacuum)
  10. customto give an oil
  11. customCrystallization from a hexane-ethyl acetate mixture (5:2 volume ratio)

Sources & evidence

ORD record
ord-b8c69f7ef4ab4beeb32e75272b4392e4
Source dataset
uspto-grants-1987_01
Patent number
US04638088

Reaction notes

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