Sodium hydride → HCID 21974597, 화합물

HRID 1247521

반응식

HRID 1247521 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>[CH3:21][O:20][C:18](=[O:19])[CH2:17][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH:5]([NH2:4])[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 21974597HCID 21974597, 화합물수율 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-9e68bece12e24000b7aff4e9a80ad1fe
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129249B2

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