Ethyl Bromide → N-Ethyl-6-methylpyridin-2-amine

HRID 1290570Notes

Reaction equation

HRID 1290570 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]([CH3:10])[CH:7]=[CH:6][CH:5]=1.[CH2:11](Br)[CH3:12]>C1(C)C=CC=CC=1>[CH2:11]([NH:3][C:4]1[N:9]=[C:8]([CH3:10])[CH:7]=[CH:6][CH:5]=1)[CH3:12]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 157652-Amino-6-methylpyridineHCID 24758Sodium hydride

Product 1

HCID 3016051N-Ethyl-6-methylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a 3000 ml dry toluene were added 185 g of 60% sodium hydride. A solution of 500 g of 6-amino-2-picoline and 500 ml of toluene were dropwise added at 60° C. over about 2 hours to the resulting dispersion. Ethyl bromide of 554 g were dropwise added at 70° 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. Thus, 632 g of 6-ethylamino-2-picoline were obtained.

Workup

  1. extractionThe organic phase was extracted
  2. washthe extract was washed two times with water
  3. concentrationconcentrated
  4. customdried

Sources & evidence

ORD record
ord-6d4201410b3a474da34238ac8a75bd42
Source dataset
uspto-grants-1998_05
Patent number
US05753017

Reaction notes

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