Methacryloyl chloride → HCID 67122696, compound

HRID 1845709Notes

Reaction equation

HRID 1845709 reaction equation
[N:1]1[CH:6]=[C:5]([CH2:7][NH2:8])[CH:4]=[C:3]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:2]=1.[C:15](Cl)(=[O:19])[C:16]([CH3:18])=[CH2:17]>ClCCl>[N:1]1[CH:6]=[C:5]([CH2:7][NH:8][C:15](=[O:19])[C:16]([CH3:18])=[CH2:17])[CH:4]=[C:3]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 13528Methacryloyl chlorideHCID 671227051-([3,3'-Bipyridin]-5-yl)methanamine

Product 1

HCID 67122696HCID 67122696, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of C-[3,3′]Bipyridinyl-5-yl-methylamine (1.16 g, 6.2 mmol) in dichloromethane (100 mL) was added methacryloyl chloride dropwise. After stirring for 7 h at ambient temperature, the reaction was quenched with 1 M NaOH, and extracted with dichloromethane (2×100 mL). The combined organics were washed with sat. NaHCO3, brine, dried with Na2SO4, and evaporated to a yellow oil (1.65 g) which was chromatographed en silica gel (pretreated with 10% triethylamine) using a methanol gradient (0-3%) in dichloromethane to give 0.76 g of clear oil.

Workup

  1. customthe reaction was quenched with 1 M NaOH
  2. extractionextracted with dichloromethane (2×100 mL)
  3. washThe combined organics were washed with sat. NaHCO3, brine
  4. dry with materialdried with Na2SO4
  5. customevaporated to a yellow oil (1.65 g) which
  6. customwas chromatographed en silica gel (pretreated with 10% triethylamine)

Sources & evidence

ORD record
ord-d49c7eb495744995867ad0e8f09f461b
Source dataset
uspto-grants-2015_02
Patent number
US08951503B2

Reaction notes

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