6-Methylpyridine-2-carbonitrile → HCID 178425254, compound

HRID 52347Notes

Reaction equation

HRID 52347 reaction equation
Cl.[CH3:2][S:3]([C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1)(=[O:5])=[O:4].C[Al](C)C.[CH3:17][C:18]1[N:23]=[C:22]([C:24]#[N:25])[CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:17][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([C:24](=[NH:25])[NH:10][C:9]2[CH:11]=[CH:12][C:6]([S:3]([CH3:2])(=[O:4])=[O:5])=[CH:7][CH:8]=2)[N:23]=1

Participants

6

Reactant 3

HCID 741826-Methylpyridine-2-carbonitrileHCID 27351804-(Methylsulfonyl)aniline hydrochlorideHCID 16682925Trimethylaluminum

Product 1

HCID 178425254HCID 178425254, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6212ChloroformSolvent

Procedure

To a suspension of 4-(methylsulfonyl)aniline hydrochloride (4.2 g, 20.3 mmol) in toluene (100 ml) at 0° C., was added trimethylaluminum (2M solution in toluene, 12 ml, 24 mmol) over 10 minutes. The reaction mixture was warmed to room temperature and stirred for 2 hours. A solution of 6-methyl-2-cyanopyridine (3.6 g, 30.5 mmol) in toluene (100 ml) was added over 10 minutes and the mixture was heated to 85°-90° C. After 24 hours, the reaction mixture was cooled to room temperature and poured over a slurry of silica gel in chloroform. After filtration, the residue was washed with a mixture of methylene chloride/methanol and later with methanol. The combined filtrates were concentrated and the resulting yellowish solid was stirred with hexane and ethyl acetate (1000 ml) and filtered. The white solid (5.1 g, 87%) was used in the next reaction without further purification. Anal. Calc'd. for C14H16N3SClO2H2O: C, 51.05, H, 5.02, N, 12.76. Found C, 50.97, H, 4.78, N, 12.80.

Workup

  1. temperaturethe mixture was heated to 85°-90° C
  2. waitAfter 24 hours
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationAfter filtration
  5. washthe residue was washed with a mixture of methylene chloride/methanol and later with methanol
  6. concentrationThe combined filtrates were concentrated
  7. stirringthe resulting yellowish solid was stirred with hexane and ethyl acetate (1000 ml)
  8. filtrationfiltered
  9. customThe white solid (5.1 g, 87%) was used in the next reaction without further purification

Sources & evidence

ORD record
ord-687814f41fff4532bd4e049a09b50873
Source dataset
uspto-grants-1997_04
Patent number
US05616601

Reaction notes

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