Sodium hydride → Methyl (3-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate

HRID 1178438ノート

反応式

HRID 1178438 の反応式
[H-].[Na+].Cl.[NH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:15].Br[CH2:17][C:18]([O:20][CH3:21])=[O:19]>CN(C=O)C>[NH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:6]1=[O:15]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 134994283-Amino-3,4-dihydroquinolin-2(1H)-one--hydrogen chloride (1/1)

生成物 1

HCID 21974597Methyl (3-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate収率 100%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60% in oil, 2.52 g, 63.0 mmol) was added to 3-amino-3,4-dihydroquinolin-2(1H)-one hydrochloride (J. Med. Chem., 28, 1985, 1511-16; 5.0 g, 25.2 mmol), in anhydrous DMF (100 mL) at 0° C. over a period of 5 min keeping the internal temperature at <10° C. The reaction was stirred for a further 30 min before addition of methyl bromoacetate (2.85 mL, 30.2 mmol), then stirred for a further 60 min. The reaction was quenched by addition of 1M aqueous HCl (5 mL) and the volatiles were removed by evaporation. The residue was dissolved in DCM (250 mL) and washed with sat. aqueous NaHCO3 (100 mL) and the organic layer was dried (MgSO4), filtered and evaporated to yield the title compound (5.89 g, 25.2 mmol) as yellow paste which was used without further purification.

後処理

  1. customat <10° C
  2. customThe reaction was quenched by addition of 1M aqueous HCl (5 mL)
  3. customthe volatiles were removed by evaporation
  4. dissolutionThe residue was dissolved in DCM (250 mL)
  5. washwashed with sat. aqueous NaHCO3 (100 mL)
  6. dry with materialthe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-8cec22b38b324106a88f024543b2549f
出典データセット
uspto-grants-2007_10
特許番号
US07276517B2

反応ノート

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