3-Amino-4-chlorophenol → HCID 136335905, compound

HRID 2266482Notes

Reaction equation

HRID 2266482 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:10][S:11]([C:14]1[CH:27]=[CH:26][C:17]([CH2:18][CH:19]([C:23](=O)[CH3:24])[C:20](=O)[CH3:21])=[CH:16][CH:15]=1)(=[O:13])=[O:12]>CS(O)(=O)=O.C1(C)C=CC=CC=1>[Cl:8][C:7]1[C:2]2[N:1]=[C:23]([CH3:24])[C:19]([CH2:18][C:17]3[CH:16]=[CH:15][C:14]([S:11]([CH3:10])(=[O:13])=[O:12])=[CH:27][CH:26]=3)=[C:20]([CH3:21])[C:3]=2[C:4]([OH:9])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 50700783-Amino-4-chlorophenolHCID 68786995HCID 68786995, compound

Product 1

HCID 136335905HCID 136335905, compound

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3-amino-4-chlorophenol (1.0 g), 3-(4-methanesulfonylbenzyl)pentane-2,4-dione (0.53 g), methanesulfonic acid (3 drops) and toluene (20 mL) was heated at reflux for 3 hours. The mixture was cooled to room temperature and the solvent removed under reduced pressure. The residue was diluted with ethyl acetate and then washed with water and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (1:0 to 99:1 by volume) gave title compound as a pale yellow solid, 0.32 g.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customthe solvent removed under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel
  8. washeluting with a mixture of dichloromethane and methanol (1:0 to 99:1 by volume)

Sources & evidence

ORD record
ord-ef2fb4552a67418b9ba1bb9ed3b84357
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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