N,N-Dimethylaniline → Ethyl 5-(4-chloro-5-phenylphthalazin-1-yl)nicotinate

HRID 593703노트

반응식

HRID 593703 반응식
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]([C:18]2[CH:19]=[N:20][CH:21]=[C:22]([CH:28]=2)[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:4][N:3]=1.O=P(Cl)(Cl)[Cl:31].CN(C)C1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:31][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]([C:18]2[CH:19]=[N:20][CH:21]=[C:22]([CH:28]=2)[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:4][N:3]=1

참가 물질

5

반응물 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178469763HCID 178469763, 화합물

생성물 1

HCID 90423764Ethyl 5-(4-chloro-5-phenylphthalazin-1-yl)nicotinate수율 95.3%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

To a solution of ethyl 5-(4-hydroxy-5-phenylphthalazin-1-yl)nicotinate (3.50 g, 9.42 mmol) in toluene (35 mL) was added POCl3 (26.4 mL, 283 mmol) followed by N,N-dimethylbenzenamine (1.5 mL, 9.42 mmol). The resulting mixture was heated in a sealed tube at 100° C. for 12 h. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and washed with saturated NaHCO3 (2×50 mL) solution. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to yield ethyl 5-(4-chloro-5-phenylphthalazin-1-yl)nicotinate (3.50 g) as a yellow solid with LC-MS purity of 47% which was taken for the next step without further purification. LCMS (Condition 12): retention time 0.97 min, [M+1]=390.0.

후처리

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (200 mL)
  4. washwashed with saturated NaHCO3 (2×50 mL) solution
  5. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-905aff003c134a3da12a68587fca853c
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242966B2

반응 노트

불러오는 중…