Hydrochloric Acid → HCID 11807225, compound

HRID 368973Notes

Reaction equation

HRID 368973 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)=[CH:6][CH:5]=[C:4]([CH3:17])[N:3]=1.Cl.[OH-].[Na+].[CH2:21]([NH2:23])[CH3:22]>>[CH2:21]([NH:23][C:2]1[C:7]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)=[CH:6][CH:5]=[C:4]([CH3:17])[N:3]=1)[CH3:22]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 14798Sodium HydroxideHCID 11053930HCID 11053930, compound

Product 1

HCID 11807225HCID 11807225, compoundYield 83%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-6-methyl-3-(3-methylbenzoyl)pyridine (2.45 g, 10 mmol) and 70% ethylamine aqueous solution (10 ml) was sealed in a tube and stirred for 4 hours at 100° C. The reaction solution was cooled to room temperature and transferred into a separating funnel. This was adjusted to pH 1 with 1 N hydrochloric acid, vigorously shaken, adjusted to pH 10 by adding 1 N sodium hydroxide aqueous solution and then extracted with chloroform. The 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 2-ethylamino-6-methyl-3-(3-methylbenzoyl)pyridine (2.10 g, 83%) 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. extractionextracted with chloroform
  6. dry with materialThe 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-d11b6ae0b9a14e06944ca4725fb4ef41
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

Loading…