Ammonia → 1-(2-fluorobenzyl)-5-(trifluoromethyl)pyridin-2(1H)-one

HRID 388272

反応式

HRID 388272 の反応式
Cl[C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][N:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:7]1=[O:16].[F:20]C(F)(F)C1C=CC(=O)NC=1.C(=O)([O-])[O-].[Na+].[Na+].BrCC1C=CC=CC=1F.N>CN(C=O)C>[F:20][C:17]1[CH:18]=[CH:19][CH:2]=[CH:3][C:4]=1[CH2:5][N:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:7]1=[O:16]

参加物

7

反応物 5

HCID 222AmmoniaHCID 10340Sodium CarbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 1474432-Hydroxy-5-(trifluoromethyl)pyridineHCID 498221301-(3-chlorobenzyl)-5-(trifluoromethyl)pyridin-2(1H)-one

生成物 1

HCID 458384511-(2-fluorobenzyl)-5-(trifluoromethyl)pyridin-2(1H)-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The preparation of 1-(3-chlorobenzyl)-5-(trifluoromethyl)pyridin-2(1H)-one includes steps of: dissolving 0.49 g (3.0 mmol) of 5-(trifluoromethyl)pyridin-2(1H)-one in 20 ml of DMF; adding 0.66 g (4.8 mmol) of sodium carbonate and 0.85 g (4.5 mmol) 1-(bromomethyl)-2-fluorobenzene; carrying out refluxing reaction for 3 hours; adding 40 ml of 15% ammonia solution; extracting by ethyl acetate (30+20+20 mL); drying by anhydrous sodium sulfate; filtering; evaporating filtrate; and separating residue by column chromatography with eluent of petroleum ether and ethyl acetate with proportion of 6:1 to obtain 0.65 of the product 1-(2-fluorobenzyl)-5-(trifluoromethyl)pyridin-2(1H)-one as a colorless oil. EI-MS (m/z): 271[M]+. 1H-NMR (CDCl3, 300 MHz): δ ppm: 5.176 (s, 2H, —CH2—), 6.623˜6.655 (d, 1H, J=9, 6 Hz, Ar—H), 7.074˜7.178 (m, 2H, Ar—H), 7.301˜7.377 (m, 1H, Ar—H), 7.410˜7.505 (m, 2H, Ar—H), 7.795 (s, 1H, Ar—H).

後処理

  1. temperaturecarrying out refluxing
  2. customreaction for 3 hours
  3. extractionextracting by ethyl acetate (30+20+20 mL)
  4. dry with materialdrying by anhydrous sodium sulfate
  5. filtrationfiltering
  6. customand separating residue by column chromatography with eluent of petroleum ether and ethyl acetate with proportion of 6:1

出典と根拠

ORDレコード
ord-ffd0b1c8b82b4ab88adf28b0cb92cda1
出典データセット
uspto-grants-2013_02
特許番号
US08377932B2

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