Lithium Hydroxide → 3,4-dihydro-2-quinolone (DHQ) derivative, 10

HRID 1376141ノート

反応式

HRID 1376141 の反応式
[Li+].[OH-].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([NH:15][CH:16]1[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:26][C:27]([O:29]C)=[O:28])[C:17]1=[O:31])=[O:14])=[CH:7]2>O.C1COCC1>[C:27]([CH2:26][N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:25][CH:16]([NH:15][C:13]([C:8]2[NH:9][C:10]3[C:6]([CH:7]=2)=[CH:5][C:4]([Cl:3])=[CH:12][CH:11]=3)=[O:14])[C:17]1=[O:31])([OH:29])=[O:28]

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 101944715-Chloro-N-[1-(methoxycarbonylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide

生成物 1

HCID 101266823,4-dihydro-2-quinolone (DHQ) derivative, 10収率 115.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

LiOH (91.5 g, 2.18 mmol) in H2O (2 mL) was added to a stirring solution of 5-chloro-N-[1-(methoxycarbonylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide (Example 1; 557 mg, 1.09 mmol) in THF (11 mL) and the reaction was stirred for 3 h. The reaction was quenched by addition of 1M aqueous HCl (40 mL) and EtOAc (60 mL) and the organic layer was dried (MgSO4), filtered and evaporated. The resultant white foam was triturated with hot Et2O (20 mL) cooled, filtered, dried and collected by filtration to afford the title compound (500 mg, 92%) as a white solid.

後処理

  1. customThe reaction was quenched by addition of 1M aqueous HCl (40 mL) and EtOAc (60 mL)
  2. dry with materialthe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe resultant white foam was triturated with hot Et2O (20 mL)
  6. temperaturecooled
  7. filtrationfiltered
  8. customdried
  9. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-76be88ee4ffd47fc93f4fc250063254f
出典データセット
uspto-grants-2007_01
特許番号
US07169927B2

反応ノート

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