Water → HCID 15041730, compound

HRID 1198831Notes

Reaction equation

HRID 1198831 reaction equation
[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18]C(=O)OCCC)=[CH:14][CH:13]=2)=[N:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[K+].O>C(O)COCCO>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)=[N:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 962Water2×HCID 14797Potassium HydroxideHCID 19867348HCID 19867348, compound

Product 1

HCID 15041730HCID 15041730, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
170 °C

Procedure

A solution of 2.24 g of propyl p-(5-pentyl-2-pyridyl)phenylcarbamate in 186 ml of diethylene glycol was treated with 26 ml of potassium hydroxide and 47 ml of water and heated at 170° C. under nitrogen. After 1.75 hours the reaction mixture was cooled, poured into 250 ml of water and extracted with methylene chloride. The organic phase was dried over sodium sulphate, filtered and freed from solvent on a rotary evaporator under a vacuum. Purification of the residue (1.39 g) by chromatography on 60 g of silica gel with 1.5 l of methylene chloride and 0.5 l of methylene chloride/ethyl acetate (vol. 4:1) and subsequent recrystallization from methylene chloride/hexane gave 0.731 g of p-(5-pentyl-2-pyridyl)aniline as yellowish crystals; m.p. 60.3°-61.3° C.

Workup

  1. temperatureAfter 1.75 hours the reaction mixture was cooled
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. filtrationfiltered
  5. customfreed from solvent on a rotary evaporator under a vacuum
  6. customPurification of the residue (1.39 g) by chromatography on 60 g of silica gel
  7. customwith 1.5 l of methylene chloride and 0.5 l of methylene chloride/ethyl acetate (vol. 4:1) and subsequent recrystallization from methylene chloride/hexane

Sources & evidence

ORD record
ord-4bf6796a407048b3ad963ba0e73d4f14
Source dataset
uspto-grants-1990_02
Patent number
US04898455

Reaction notes

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