Pyridine → HCID 19165311, 화합물

HRID 963019노트

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HRID 963019 반응식
[CH:1]1[C:13]2[CH:12]([C:14]([OH:16])=O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.N1C=CC=CC=1>C(Cl)Cl.CN(C=O)C.C(OCC)(=O)C.O>[C:24]1([CH2:23][NH:30][C:14]([CH:12]2[C:13]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6]3[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=3)=[O:16])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

참가 물질

9

반응물 4

HCID 1049PyridineHCID 7504BenzylamineHCID 65578Oxalyl chlorideHCID 748099-Carboxyfluorene

생성물 1

HCID 19165311HCID 19165311, 화합물수율 86.9%

시약·촉매·용매 4

HCID 6228Dimethylformamide촉매HCID 962Water용매HCID 6344Dichloromethane용매3회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

A solution of 9-fluorene carboxylic acid (2.10 g, 10.0 mmol) in 50 mL of CH2Cl2 was treated with oxalyl chloride in dichloromethane (6.0 mL, 12.0 mmol) and two drops of DMF. After 0.75 h, the mixture was concentrated under reduced pressure to give a white solid. The solid was diluted with 50 mL of CH2Cl2, cooled to 0° C., treated with benzylamine (1.17 g, 11.0 mmol) and pyridine (0.87 g, 11 mmol). The transparent yellow solution was stirred for 3 h at room temperature and diluted with ethyl acetate and water. The organic fraction was dried over Na2SO4 and concentrated to a white solid. The solid purified by trituration with hexanes and recrystalization from hot methanol to give 2.60 g (86%) of title compound as white flakes. mp 195°-200° C.

후처리

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto give a white solid
  3. dry with materialThe organic fraction was dried over Na2SO4
  4. concentrationconcentrated to a white solid
  5. customThe solid purified by trituration with hexanes and recrystalization from hot methanol

출처 및 근거

ORD 기록
ord-aa8327bf931f478c9a3244afd183fd65
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05760246

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