Dimethylformamide → 3-(3-Pyridyl)acryloyl chloride hydrochloride

HRID 1754110Notes

Reaction equation

HRID 1754110 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][C:9]([OH:11])=O)[CH:2]=1.C(Cl)(=O)C([Cl:15])=O.CN(C=O)C>C(Cl)Cl>[ClH:15].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][C:9]([Cl:15])=[O:11])[CH:2]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1019843-(3-Pyridinyl)-2-propenoic acid

Product 1

HCID 713600273-(3-Pyridyl)acryloyl chloride hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-(pyridin-3-yl)acrylic acid (1.03 g, 6.9 mmol) in DCM (25 ml) is added oxalyl chloride (2 M in DCM, 17.25 mL, 34.5 mmol) dropwise. With stir, 100 uL of DMF is added and the mixture is stirred at RT for 30 min then heat at reflux for 3 h. The solvent is removed under vacuum and ether is added (40 mL). The suspension is stirred at RT for 30 min then filtered. The solid is washed with ether (20 mL) and dried under vacuum to give the tilted compound as a white solid. (1.22 g, 87%).

Workup

  1. stirringthe mixture is stirred at RT for 30 min
  2. temperaturethen heat
  3. temperatureat reflux for 3 h
  4. customThe solvent is removed under vacuum and ether
  5. additionis added (40 mL)
  6. stirringThe suspension is stirred at RT for 30 min
  7. filtrationthen filtered
  8. washThe solid is washed with ether (20 mL)
  9. customdried under vacuum

Sources & evidence

ORD record
ord-1fabd8942d834f34ab15fd3434f78183
Source dataset
uspto-grants-2015_10
Patent number
US09169209B2

Reaction notes

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