Methylamine → 3-Acetyl-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4(1H)-one

HRID 2058866ノート

反応式

HRID 2058866 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH2:9][C:10](=[O:15])[CH2:11][C:12](=[O:14])[CH3:13])[CH:6]=[CH:7][CH:8]=1.CO[CH:20](OC)[N:21]([CH3:23])[CH3:22].CN>>[C:12]([C:11]1[C:10](=[O:15])[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:16])([F:17])[F:1])[CH:4]=2)=[CH:22][N:21]([CH3:23])[CH:20]=1)(=[O:14])[CH3:13]

参加物

4

反応物 3

HCID 6329MethylamineHCID 78373Dimethylformamide dimethyl acetalHCID 132018031-[3-(Trifluoromethyl)phenyl]pentane-2,4-dione

生成物 1

HCID 132018103-Acetyl-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4(1H)-one

実験手順

Ten g. of 1-(3-trifluoromethylphenyl)-2,4-pentanedione was reacted with 40 ml. of N,N-dimethylformamide dimethyl acetal, and then with 10 ml. of 40% aqueous methylamine, as described in the examples above. The reaction mixture was evaporated under vacuum, and the residue was taken up in 1.5 liters of dichloromethane. The solution was washed with 1 liter of water, and the organic layer was dried with magnesium sulfate, treated with activated charcoal, filtered and evaporated under vacuum. The residue was triturated under diisopropyl ether, and a yellow powdery solid crystallized. The solid was found to be 4.56 g. of the desired product, m.p. 130°-131°, showing the following peaks in nmr analysis: δ8.10 (d, J=3 Hz, H2 of pyridine); 8.0-7.3 (m, 4H, aromatic); 7.43 (d, J=3 Hz, H6 of pyridine); 3.77 (s, 3H, N--CH3); 2.73 (s, 3H, COCH3).

後処理

  1. customThe reaction mixture was evaporated under vacuum
  2. washThe solution was washed with 1 liter of water
  3. dry with materialthe organic layer was dried with magnesium sulfate
  4. additiontreated with activated charcoal
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe residue was triturated under diisopropyl ether
  8. customa yellow powdery solid crystallized

出典と根拠

ORDレコード
ord-57bb0ef115614bd1864cfa6c709f876a
出典データセット
uspto-grants-1982_03
特許番号
US04319916

反応ノート

読み込み中…