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

HRID 1178438

반응식

HRID 1178438 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8cec22b38b324106a88f024543b2549f
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276517B2

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