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

HRID 593703ノート

反応式

HRID 593703 の反応式
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

参加物

5

反応物 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178469763HCID 178469763、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-905aff003c134a3da12a68587fca853c
出典データセット
uspto-grants-2016_01
特許番号
US09242966B2

反応ノート

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