Triethylamine → Ethyl 2-(E-2-(4-(N,N-dimethylaminomethyl)phenyl)ethen-1-yl)nicotinate

HRID 2421298Notes

Reaction equation

HRID 2421298 reaction equation
Cl[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:13][N:14]([CH2:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[CH2:22])=[CH:19][CH:18]=1)[CH3:15].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:15][N:14]([CH2:16][C:17]1[CH:18]=[CH:19][C:20](/[CH:21]=[CH:22]/[C:2]2[N:12]=[CH:11][CH:10]=[CH:9][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:23][CH:24]=1)[CH3:13]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 519956Benzenemethanamine, ar-ethenyl-N,N-dimethyl-HCID 2796614Ethyl chloronicotinate

Product 1

HCID 11811059Ethyl 2-(E-2-(4-(N,N-dimethylaminomethyl)phenyl)ethen-1-yl)nicotinateYield 33.9%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

6.7 g (39 mmol) of ethyl 2-chloronicotinate, 8.2 g (51 mmol) of 4-(N,N-dimethylaminomethyl)styrene, 9.9 g (98 mmol) of triethylamine, 0.36 g of palladium(II) acetate and 0.96 [lacuna] of tri(o-tolyl)phosphine were mixed in 150 ml of dimethylformamide and, after addition of 1 ml of water, stirred at 140° C. for 13 h. The reaction mixture was then concentrated in vacuo, and the resulting residue was partitioned between ethyl acetate and water. The organic phase was separated off, washed with water, dried and concentrated in vacuo. The residue was then crystallized as oxalate from isopropanol after addition of an equivalent amount of oxalic acid. 4.1 g (27%) of the product were obtained as monooxalate.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe resulting residue was partitioned between ethyl acetate and water
  3. customThe organic phase was separated off
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was then crystallized as oxalate from isopropanol
  8. additionafter addition of an equivalent amount of oxalic acid

Sources & evidence

ORD record
ord-bf8e8048d2f14b29b98be019a5db11bb
Source dataset
uspto-grants-2011_06
Patent number
US07956093B2

Reaction notes

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