Ethyl Bromide → 6-diethylamino-2-picoline

HRID 1290571Notes

Reaction equation

HRID 1290571 reaction equation
[H-].[Na+].[CH2:3]([NH:5][C:6]1[N:11]=[C:10]([CH3:12])[CH:9]=[CH:8][CH:7]=1)[CH3:4].[CH2:13](Br)[CH3:14]>C1(C)C=CC=CC=1>[CH2:3]([N:5]([CH2:13][CH3:14])[C:6]1[N:11]=[C:10]([CH3:12])[CH:9]=[CH:8][CH:7]=1)[CH3:4]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 3016051N-Ethyl-6-methylpyridin-2-amine

Product 1

HCID 110301706-diethylamino-2-picoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
93 °C

Procedure

To a 3000 ml dry toluene were added 185 g of 60% sodium hydride. A solution of 632 g of 6-ethylamino-2-picoline and 500 ml of toluene was dropwise added at 90° C. over about 2 hours to the resulting dispersion and stirred at 93° C. for additional one hour. Ethyl bromide of 554 g were dropwise added at 90° C. over about 2 hours to the resulting mixture and stirred for additional one hour. The reation mixture was added to 3000 ml of ice water. The organic phase was extracted and the extract was washed two times with water, concentrated and dried. The product obtained above was evaporated under reduced pressure (7 mmHg). Thus, 630 g of 6-diethylamino-2-picoline (bp7 103-108) were obtained.

Workup

  1. stirringstirred for additional one hour
  2. extractionThe organic phase was extracted
  3. washthe extract was washed two times with water
  4. concentrationconcentrated
  5. customdried
  6. customThe product obtained
  7. customabove was evaporated under reduced pressure (7 mmHg)

Sources & evidence

ORD record
ord-0c161e0ae80642db84337288ff60b302
Source dataset
uspto-grants-1998_05
Patent number
US05753017

Reaction notes

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