Dimethylformamide → HCID 58424954, compound

HRID 2409427Notes

Reaction equation

HRID 2409427 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:25][CH:24]=1>ClCCl.C(N(CC)CC)C>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:27][CH:28]=1)=[O:6]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 762582-Chloronicotinic acidHCID 10442595Ethyl 3-(4-aminophenyl)propanoate

Product 1

HCID 58424954HCID 58424954, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

2-Chloronicotinic acid (1 g, 6.35 mmol) was dissolved in dichloromethane and added with oxalylchloride and a catalytic amount of N,N-dimethylformamide at 0° C. The resulting mixture was refluxed for 3 hours and concentrated under reduced pressure. And then, the obtained acid chloride was dissolved in dichloromethane and cooled to 0° C. Ethyl 3-(4-nitrophenyl)acrylate (1.35 g, 7 mmol) prepared in step 1 and triethylamine were added, and the reaction mixture was stirred at room temperature for 12 hours. The mixture was extracted with chloroform, dried over anhydrous magnesium sulfate, and concentrated to dryness. The residue then was purified by flash column chromatography (chloroform:methanol=10:1) to obtain the title compound (2.1 g, yield: 92%, colorless liquid).

Workup

  1. customat 0° C
  2. temperatureThe resulting mixture was refluxed for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. dissolutionAnd then, the obtained acid chloride was dissolved in dichloromethane
  5. extractionThe mixture was extracted with chloroform
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated to dryness
  8. customThe residue then was purified by flash column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-9a0cf5c824604b2d9e989b03815bd740
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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