Aniline → HCID 1481283、化合物

HRID 1407080ノート

反応式

HRID 1407080 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Al](C)C.[O:12]=[C:13]1[CH:18]=[CH:17][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[N:15]=[C:14]1[C:29]([O:31]C)=O>C(Cl)Cl>[O:12]=[C:13]1[CH:18]=[CH:17][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=2)[N:15]=[C:14]1[C:29]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:31]

参加物

5

反応物 3

HCID 6115AnilineHCID 1481306HCID 1481306、化合物HCID 16682925Trimethylaluminum

生成物 1

HCID 1481283HCID 1481283、化合物収率 30%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of aniline (0.360 mL, 3.95 mmol) in methylene chloride (10 mL) was cooled on an ice water bath then treated with a solution of trimethyl aluminum (2 M in toluene, 2.0 mL, 4.0 mmol). After the addition was complete, the reaction was allowed to warm to room temperature and stirred for 30 min. At that point, methyl 4-oxo-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carboxylate (0.595 g, 2.00 mmol) was added and the reaction was heated at reflux for 18 h. After that time, the reaction was cooled to room temperature and carefully quenched with HCl aqueous solution (1 N, 5 mL). The organic layer was separated and the aqueous layer was extracted with methylene chloride (3×10 mL). The combined organic extracts were washed with saturated NaHCO3 aqueous solution (50 mL) and brine (50 mL), dried (MgSO4), and concentrated. The residue was recrystallized from ethyl acetate/hexanes to give 0.214 g (30%) of 4-oxo-N-phenyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carboxamide as yellow crystals.

後処理

  1. additionAfter the addition
  2. temperaturethe reaction was heated
  3. temperatureat reflux for 18 h
  4. temperatureAfter that time, the reaction was cooled to room temperature
  5. customcarefully quenched with HCl aqueous solution (1 N, 5 mL)
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with methylene chloride (3×10 mL)
  8. washThe combined organic extracts were washed with saturated NaHCO3 aqueous solution (50 mL) and brine (50 mL)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customThe residue was recrystallized from ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-4e1eb7615996426b9cc1fc3f7170b512
出典データセット
uspto-grants-2014_12
特許番号
US08916566B2

反応ノート

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