Hydrochloric Acid → 3-(3-Chlorobenzoyl)-6-ethyl-2-ethylaminopyridine

HRID 368970Notes

Reaction equation

HRID 368970 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)=[CH:6][CH:5]=[C:4]([CH2:17][CH3:18])[N:3]=1.[CH2:19]([NH2:21])[CH3:20].Cl.[OH-].[Na+]>>[Cl:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[C:8]([C:7]1[C:2]([NH:21][CH2:19][CH3:20])=[N:3][C:4]([CH2:17][CH3:18])=[CH:5][CH:6]=1)=[O:16]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 14798Sodium HydroxideHCID 232844892-Chloro-3-(3-chlorobenzoyl)-6-ethylpyridine

Product 1

HCID 154805223-(3-Chlorobenzoyl)-6-ethyl-2-ethylaminopyridineYield 76%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-3-(3-chlorobenzoyl)-6-ethylpyridine (3.4 g, 12 mmol) and 70% ethylamine aqueous solution (15 ml) was sealed in a tube and stirred at 100° C. for 4 hours. The reaction solution was cooled to room temperature and then transferred into a separating funnel. This was acidified by adding 1 N hydrochloric acid, vigorously shaken and then alkalified by adding 1 N sodium hydroxide aqueous solution. This was extracted with chloroform, the resulting organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate was removed by filtration and then the filtrate was concentrated under a reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 3-(3-chlorobenzoyl)-6-ethyl-2-ethylaminopyridine (2.6 g, 76%) as a yellow oily material.

Workup

  1. customwas sealed in a tube
  2. temperatureThe reaction solution was cooled to room temperature
  3. customtransferred into a separating funnel
  4. stirringvigorously shaken
  5. extractionThis was extracted with chloroform
  6. dry with materialthe resulting organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate
  7. customwas removed by filtration
  8. concentrationthe filtrate was concentrated under a reduced pressure
  9. customThereafter, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-4e2539f478604166b70c6564becfdf9f
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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