Dimethylamine → 7-Chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide

HRID 1887792ノート

反応式

HRID 1887792 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[C:7]([CH3:21])=[C:8]([C:18](O)=[O:19])[N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)[N:32]1[CH2:36]CC[CH2:33]1.C(N(CC)C(C)C)(C)C.CNC>CN(C=O)C>[CH3:33][N:32]([CH3:36])[C:18]([C:8]1[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]2[C:5]([C:6](=[O:22])[C:7]=1[CH3:21])=[CH:4][CH:3]=[C:2]([Cl:1])[CH:11]=2)=[O:19]

参加物

6

反応物 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 712085077-Chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid

生成物 1

HCID 712089157-Chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide収率 110%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In a 50 mL round bottom flask, 7-chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid (0.5 g, 1.60 mmol), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBrOP, 1.11 g, 2.39 mmol) and N,N-diisopropylethylamine (1.11 mL, 6.37 mmol) were added to anhydrous DMF (5.0 mL). The mixture was stirred at room temperature for 30 min. Dimethylamine (2M in THF, 1.6 mL, 3.2 mmol) was added and the reaction mixture was stirred at room temperature for 48 hr. The mixture was concentrated to dryness and the crude was purified by flash chromatography using 3:2 hexane-ethyl acetate to afford 7-chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide (600 mg, >100% yield). MS calcd for C19H17ClN2O2 [(M+H)+] 341, obsd 341.

後処理

  1. stirringthe reaction mixture was stirred at room temperature for 48 hr
  2. concentrationThe mixture was concentrated to dryness
  3. customthe crude was purified by flash chromatography

出典と根拠

ORDレコード
ord-83ac3126b6184a8aa7cf7c031edb12d5
出典データセット
uspto-grants-2013_08
特許番号
US08501732B2

反応ノート

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