2-Amino-4-methylphenol → 2'-Hydroxy-5'-methyl-4-(4-phenylbutoxy)benzanilide

HRID 982217Notes

Reaction equation

HRID 982217 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=1[OH:29]>CN(C)C=O.C(Cl)Cl.C(Cl)(=O)C(Cl)=O.N1C=CC=CC=1>[OH:29][C:23]1[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:22]=1[NH:21][C:16](=[O:18])[C:15]1[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 2

HCID 72642-Amino-4-methylphenolHCID 110438254-(4-Phenylbutoxy)benzoic Acid

Product 1

HCID 151065462'-Hydroxy-5'-methyl-4-(4-phenylbutoxy)benzanilideYield 100.8%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×HCID 65578Oxalyl chlorideSolvent

Procedure

One drop of N,N-dimethylformamide was added to a solution of 1 g of p-(4-phenylbutoxy)benzoic acid in 5 ml of methylene chloride and 2 ml of oxalyl chloride was added to the mixture at -30° C. or lower. The mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure to obtain crude p-(4-phenylbutoxy)benzoyl chloride. This substance was dissolved in 5 ml of methylene chloride and the resulting solution was added to a solution of 1 g of 2-amino-4-methylphenol in 5 ml of pyridine under ice cooling followed by stirring at room temperature for 3 hours. The reaction mixture was poured into conc. hydrochloric acid-ice and then extracted with ethyl acetate. The extract was washed subsequently with water, an aqueous solution of sodium hydrogen carbonate and again water. After drying over anhydrous magnesium sulfate, the system was concentrated under reduced pressure to obtain 1.4 g of 2'-hydroxy-5'-methyl-4-(4-phenylbutoxy)benzanilide.

Workup

  1. additionwas added to the mixture at -30° C.
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto obtain crude p-(4-phenylbutoxy)benzoyl chloride
  4. stirringby stirring at room temperature for 3 hours
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed subsequently with water
  7. dry with materialAfter drying over anhydrous magnesium sulfate
  8. concentrationthe system was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c0a13a5b193e4057893b9351a46c16b2
Source dataset
uspto-grants-1991_02
Patent number
US04994479

Reaction notes

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