Aniline → HCID 1481283, 화합물

HRID 1407080노트

반응식

HRID 1407080 반응식
[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]

참가 물질

5

반응물 3

HCID 6115AnilineHCID 1481306HCID 1481306, 화합물HCID 16682925Trimethylaluminum

생성물 1

HCID 1481283HCID 1481283, 화합물수율 30%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4e1eb7615996426b9cc1fc3f7170b512
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916566B2

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