Pyridine → HCID 23333570, compound

HRID 1076761Notes

Reaction equation

HRID 1076761 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[CH2:14](I)[CH3:15].N1C=CC=CC=1>C(O)(C)C>[CH2:14]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1)[CH3:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6340IodoethaneHCID 225219p-Aminophenylacetic acid ethyl ester

Product 1

HCID 23333570HCID 23333570, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Ethyl p-aminophenylacetate (5.4 g), ethyl iodide (4.7 g), pyridine (2.4 g) and isopropanol (50 ml) are boiled together during 6 hours. The reaction mixture is concentrated in vacuo, taken up into water, extracted with ether and dried, and the solvent is then removed. Ethyl p-ethylaminophenylacetate (2 g) is isolated by chromatography over silica. Saponification in the cold, in methanolic sodium hydroxide, gives 1.2 g of p-ethylaminophenylacetic acid. M.p. inst. = 123°C after recrystallization from ethyl acetate.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. extractionextracted with ether
  3. customdried
  4. customthe solvent is then removed

Sources & evidence

ORD record
ord-73c28a3649ec4e34a1b0fd3e403dc777
Source dataset
uspto-grants-1976_05
Patent number
US03957850

Reaction notes

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