HCID 66704043, compound → HCID 16742539, compound

HRID 425260Notes

Reaction equation

HRID 425260 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:19])[CH:8]=2)[N:3]=1>O.C(O)C.[Na].[Hg]>[NH2:1][C:2]1[CH2:11][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:19])[CH:8]=2)[N:3]=1

Participants

5

Reactant 1

HCID 66704043HCID 66704043, compound

Product 1

HCID 16742539HCID 16742539, compound

Reagents, catalysts & solvents 3

HCID 9837419Sodium amalgamCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

6.76 g of sodium amalgam were added over the course of one hour to a solution of 255 mg of 2-amino-6-chloro-4-(4-aminophenyl)quinoline in 3.4 ml of water and 22 ml of ethanol while stirring. The mixture was stirred overnight and decanted off from the Hg precipitate, and the solvent was removed by distillation under reduced pressure. After carrying out an MPLC column chromatography in a mixture of 10 parts by volume of ethyl acetate, 5 parts by volume of methanol, 5 parts by volume of n-heptane, 5 parts by volume of dichloromethane and 1 part by volume of ammonia (concentrated) and acidification with a little concentrated hydrochloric acid, the solvent was removed by distillation and the residue was induced to crystallize with a little ethyl acetate.

Workup

  1. stirringThe mixture was stirred overnight
  2. customdecanted off from the Hg precipitate
  3. customthe solvent was removed by distillation under reduced pressure
  4. additionin a mixture of 10 parts by volume of ethyl acetate, 5 parts by volume of methanol, 5 parts by volume of n-heptane, 5 parts by volume of dichloromethane and 1 part by volume of ammonia (concentrated) and acidification with a little concentrated hydrochloric acid
  5. customthe solvent was removed by distillation
  6. customto crystallize with a little ethyl acetate

Sources & evidence

ORD record
ord-49abe0c90416417ea2286fdc78790dc0
Source dataset
uspto-grants-2012_01
Patent number
US08106204B2

Reaction notes

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