Hydrochloric Acid → 2-Diacetylamino-4-(4-methylphenyl)pyridine

HRID 352785Notes

Reaction equation

HRID 352785 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.[C:24](Cl)(=[O:26])[CH3:25].Cl.[C:29](OCC)(=[O:31])[CH3:30]>ClCCl.CO>[C:24]([N:1]([C:29](=[O:31])[CH3:30])[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1)(=[O:26])[CH3:25]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chloride2×HCID 8857Ethyl AcetateHCID 81531Diisopropylethylamine2×HCID 137770672-Amino-4-(4-methylphenyl)pyridine

Product 1

HCID 227105062-Diacetylamino-4-(4-methylphenyl)pyridineYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2-Amino-4-(4-methylphenyl)pyridine (1.27 g) was dissolved in dichloromethane (50 ml). Under ice cooling, N,N-diisopropylethylamine (1.80 ml) and acetyl chloride (735 μl) were successively added dropwise to the resulting solution. After heating to room temperature, the reaction mixture was added again with N,N-diisopropylethylamine (0.90 ml) and acetyl chloride (800 μl). The mixture was stirred for 18 hours. Methanol was added to the reaction mixture. Dilute hydrochloric acid and ethyl acetate were then added to the residue obtained by distilling off the solvent in order to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, followed by concentration. The residue was dissolved in methanol. Crystals precipitated by the addition of water were collected by filtration and dried, whereby the title compound (1.39 g, 75%) was obtained.

Workup

  1. customobtained
  2. distillationby distilling off the solvent in order
  3. customto separate the organic layer
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationfollowed by concentration
  6. dissolutionThe residue was dissolved in methanol
  7. customCrystals precipitated by the addition of water
  8. filtrationwere collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-e209f9738eaf47d882b2eee33a0043f3
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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