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

HRID 353426

반응식

HRID 353426 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
140 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-474cc3efaa0f4b238426448106145851
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06753327B1

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