Pyridine → HCID 19165311、化合物

HRID 963019ノート

反応式

HRID 963019 の反応式
[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

参加物

9

反応物 4

HCID 1049PyridineHCID 7504BenzylamineHCID 65578Oxalyl chlorideHCID 748099-Carboxyfluorene

生成物 1

HCID 19165311HCID 19165311、化合物収率 86.9%

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-aa8327bf931f478c9a3244afd183fd65
出典データセット
uspto-grants-1998_06
特許番号
US05760246

反応ノート

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