Hydrochloric Acid → HCID 10221444, compound

HRID 1635510Notes

Reaction equation

HRID 1635510 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=O)[CH2:9][C:10](=O)[CH3:11])[CH:5]=[CH:4][N:3]=1.[C:14]1([CH3:22])[CH:19]=[CH:18][C:17]([NH:20][NH2:21])=[CH:16][CH:15]=1.Cl.C(N(CC)CC)C>CO>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:20]([C:17]3[CH:18]=[CH:19][C:14]([CH3:22])=[CH:15][CH:16]=3)[N:21]=[C:10]([CH3:11])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10875(4-Methylphenyl)hydrazineHCID 18676105HCID 18676105, compound

Product 1

HCID 10221444HCID 10221444, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(2-chloro-4-pyridinyl)-1,3-butanedione (7 g, 35.25 mmol), paratolylhydrazine.HCl (6.13 g, 38.78 mmol) and triethylamine (5.41 mL, 38.78 mmol) in methanol (100 mL) was heated to reflux overnight. The resulting dark colored solution was cooled to room temperature and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate and brine, and dried over magnesium sulfate. After filtration, the solution was concentrated to give a brown solid. The solid was purified by column chromatography (silica gel, 2:8 EtOAc/hexane) to yield the titled product (3.6 g, 52%) as a crystalline light brown solid. MP: 100.07° C. Anal. Calc'd for C16H14N3Cl: C, 67.72, H, 4.97, N, 14.81. Found: C 67.40, H, 4.89, N, 14.59.

Workup

  1. temperatureto reflux overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe solution was concentrated
  7. customto give a brown solid
  8. customThe solid was purified by column chromatography (silica gel, 2:8 EtOAc/hexane)

Sources & evidence

ORD record
ord-b32731eae3354fd281752e9a3665a0bb
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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