Pyridine → HCID 19815939, compound

HRID 2247874Notes

Reaction equation

HRID 2247874 reaction equation
[NH2:1][C:2]1[C:3]([CH3:22])=[N:4][C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[CH:9]=1.N1C=CC=CC=1.[Cl:29][CH2:30][CH2:31][C:32](Cl)=[O:33].[OH-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.CN(C)C=O>[Cl:29][CH2:30][CH2:31][C:32]([NH:1][C:2]1[C:3]([CH3:22])=[N:4][C:5]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[CH:9]=1)=[O:33]

Participants

8

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 693643-Chloropropionyl chlorideHCID 19815934HCID 19815934, compound

Product 1

HCID 19815939HCID 19815939, compoundYield 60.7%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-amino-4-(3-cyanophenyl)-2-methyl-6-phenylpyridine (0.6 g) and pyridine (0.2 g) in toluene (10 ml) was added 3-chloropropionyl chloride (0.32 g) at 0° C. The mixture was stirred at the same temperature for 30 minutes and further at ambient temperature for 6 hours. After the mixture was allowed to stand at ambient temperature for 3 days, N,N-dimethylformamide (10 ml) was added thereto to dissolve the precipitates. The mixture was stirred at ambient temperature for 5 hours, diluted with ice-cold water (50 ml) and ethyl acetate (50 ml), and adjusted to pH 10 with 5N sodium hydroxide. The separated organic layer was washed with brine, dried and concentrated in vacuo. The residue was triturated with diisopropyl ether to give 3-(3-chloropropionylamino)-4-(3-cyanophenyl)-2-methyl-6-phenylpyridine (0.48 g).

Workup

  1. waitto stand at ambient temperature for 3 days
  2. dissolutionto dissolve the precipitates
  3. stirringThe mixture was stirred at ambient temperature for 5 hours
  4. washThe separated organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-e609374cb09f4305b231618ba20400f1
Source dataset
uspto-grants-1991_08
Patent number
US05037824

Reaction notes

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