Pyridine → HCID 12764110, compound

HRID 1577639Notes

Reaction equation

HRID 1577639 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[NH:5][C:6](=[O:9])[CH2:7][Br:8].[C:13](Cl)(=[O:16])[CH2:14][CH3:15].N1C=CC=CC=1>C(Cl)Cl>[C:13]([O:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[NH:5][C:6](=[O:9])[CH2:7][Br:8])(=[O:16])[CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 127641052-Bromo-N-(3-hydroxyphenyl)acetamide

Product 1

HCID 12764110HCID 12764110, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The anilide, 3'-hydroxy bromoacetanilide, 6.9 g. and propionyl chloride (3.1 g., 0.033 mole) are combined in 120 ml. of methylene chloride as a solvent. Pyridine (2.6 g., 0.033 mole) is added dropwise. A slightly exothermic reaction takes place during the addition. Stirring is continued at room temperature for 20 minutes. A clear solution is obtained. The material is washed sucessively with water, dilute hydrochloric acid and again with water. The organic layer is dried over anhydrous magnesium sulfate and the solvent evaporated. The resulting material is recrystallized from a mixture of ethylacetate and ether. There is obtained 6.5 g. of the title compound, m.p. 85°-88° C.

Workup

  1. customA slightly exothermic reaction
  2. additionduring the addition
  3. customA clear solution is obtained
  4. washThe material is washed sucessively with water, dilute hydrochloric acid and again with water
  5. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  6. customthe solvent evaporated
  7. customThe resulting material is recrystallized from a mixture of ethylacetate and ether
  8. customThere is obtained 6.5 g

Sources & evidence

ORD record
ord-3c7133f5acbe408cbcd6b0716849d231
Source dataset
uspto-grants-1981_09
Patent number
US04288605

Reaction notes

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