HCID 19030722, compound → HCID 19030970, compound

HRID 1648543Notes

Reaction equation

HRID 1648543 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][C:11]2=[O:12])=[CH:6][CH:5]=1)([O-])=O>[Pd].C(O)(=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][C:11]2=[O:12])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 19030722HCID 19030722, compound

Product 1

HCID 19030970HCID 19030970, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To 10 % Pd-C (0.1 g) is added acetic acid (20 ml) and then 1-(4-nitrophenyl)carbostyril (0.9 g) and the mixture is subjected to catalytic reduction at 80° C. under normal pressure. After completion of the reaction, 10 % Pd--C is removed by filtration and the resulting solution is concentrated under reduced pressure. To the concentrate is added water and the solution is made alkaline with an aqueous sodium hydroxide solution and then extracted with dichloromethane. The extract is washed with water and dried over magnesium sulfate. The solvent is distilled off under reduced pressure and the residue is purified by silica gel column chromatography and recrystallized from ethanol to give 1-(4-aminophenyl)carbostyril (0.66 g) as brown powders, m.p. 225°-230° C.

Workup

  1. customis subjected to catalytic reduction at 80° C. under normal pressure
  2. customis removed by filtration
  3. concentrationthe resulting solution is concentrated under reduced pressure
  4. additionTo the concentrate is added water
  5. extractionextracted with dichloromethane
  6. washThe extract is washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent is distilled off under reduced pressure
  9. customthe residue is purified by silica gel column chromatography
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-eedbfe3bea124e9dba6ff6ac531a01a3
Source dataset
uspto-grants-1995_07
Patent number
US05436254

Reaction notes

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