6-Methyl-3-pyridinecarboxaldehyde → HCID 46842009, compound

HRID 1846356Notes

Reaction equation

HRID 1846356 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:27]=[CH:26][CH:25]=[CH:24][C:12]=1[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=1)=[O:14]>CCO>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([C:6]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=3)[C:13](=[O:14])[C:12]3[C:11](=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:10]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 101925666-Methyl-3-pyridinecarboxaldehydeHCID 20121372HCID 20121372, compound

Product 1

HCID 46842009HCID 46842009, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-methylnicotinaldehyde (0.36 g, 3.0 mmol), 2-amino-N-(4-(methylthio)phenyl)benzamide (3.0 mmol), and anyhydrous CuCl2 (0.80 g, 6.0 mmol) in anyhydrous EtOH was refluxed for 6 hours. After concentration in vacuo, the residue was redissolved in EtOAc and washed with H2O, then brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 0% to 20% MeOH in CH2Cl2, followed by 40% to 100% of 92:7:1 CHCl3/MeOH/concentrate NH4OH in CH2Cl2, afforded the title compound (19%). 1H-NMR (300 MHz, DMSO-d6): δ8.42 (s, 1H), 8.20 (d, J=7.9 Hz, 1H), 7.87-7.97 (m, 1H), 7.78 (d, J=8.1 Hz, 1H), 7.56-7.73 (m, 2H), 7.31 (d, J=8.3 Hz, 2H), 7.10-7.26 (m, 3H), 2.43 (s, 3H), 2.41 (s, 3H). MS (APCI) m/z: 360 (M+H)+.

Workup

  1. temperaturewas refluxed for 6 hours
  2. concentrationAfter concentration in vacuo
  3. dissolutionthe residue was redissolved in EtOAc
  4. washwashed with H2O
  5. dry with materialbrine, dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel
  9. washeluting with 0% to 20% MeOH in CH2Cl2
  10. concentrationconcentrate NH4OH in CH2Cl2

Sources & evidence

ORD record
ord-190ed8c7e20c43c7b89b64acb88032ad
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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