N,N-Dimethylaniline → Methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate

HRID 717023ノート

反応式

HRID 717023 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17](=O)[NH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:19]([O:21][CH3:22])=[O:20])[CH:14]=3)[NH:9]2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:25].CN(C)C1C=CC=CC=1>>[Cl:25][C:17]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:9][C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([C:19]([O:21][CH3:22])=[O:20])=[CH:12][CH:11]=2

参加物

4

反応物 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 67041991Methyl 2-(4-fluorophenyl)-3-oxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

生成物 1

HCID 77231184Methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate

反応条件

温度
110 °C

実験手順

Into a 100-mL round-bottom flask, was placed methyl 2-(4-fluorophenyl)-3-oxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate (1.2 g, 4.00 mmol, 1.00 equiv), POCl3 (12.2 g, 80.26 mmol, 20.00 equiv), N,N-dimethylbenzenamine (4.9 g, 40.50 mmol, 10.00 equiv). The resulting solution was stirred for overnight at 110° C. in an oil bath. The resulting mixture was concentrated under vacuum and diluted with 50 mL of water. The pH value of the aqueous solution was adjusted to 7 with sodium bicarbonate (4 mol/L). The resulting mixture was concentrated under vacuum and purified by silica gel chromatography with ethyl acetate/petroleum ether (1:40).

後処理

  1. customInto a 100-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. additiondiluted with 50 mL of water
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. custompurified by silica gel chromatography with ethyl acetate/petroleum ether (1:40)

出典と根拠

ORDレコード
ord-7f776f6c5c98477d97e18d2ed490188f
出典データセット
uspto-grants-2015_11
特許番号
US09193693B2

反応ノート

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