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

HRID 1887790

반응식

HRID 1887790 반응식
[CH3:1][O:2][C:3](=[O:24])[C:4]([N:6]([C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20](=[O:23])[CH2:21][CH3:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.C(=O)([O-])[O-].[K+].[K+].CCCCCC>CO.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:4]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]2[C:14]([C:20](=[O:23])[C:21]=1[CH3:22])=[CH:15][CH:16]=[C:17]([Cl:19])[CH:18]=2)=[O:24]

참가 물질

6

반응물 3

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 70816656HCID 70816656, 화합물

생성물 1

HCID 708166537-Chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester수율 73.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매2회

반응 조건

온도
80 °C

실험 절차

To a stirred suspension of N-(5-chloro-2-propionyl-phenyl)-N-phenyl-oxalamic acid methyl ester (15.0 g, 43.5 mmol) in methanol (200 mL) was added potassium carbonate (35.0 g, 253 mmol) at room temperature. The mixture was heated at 80° C. for 1 hr. Completion of the reaction was monitored by silica TLC (mobile phase; hexane:ethyl acetate=7:3; Rf=0.6). The reaction mixture was cooled to room temperature. The reaction mixture was filtered through a sintered glass funnel and the solids were washed with MeOH (2×50 mL). The combined filtrates were concentrated under reduced pressure. The residue obtained was taken up in ethyl acetate (500 mL), washed with water (2×200 mL), dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude material was purified by washing with a mixture of hexane-ether to afford 7-chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (10.5 g, 73.4% yield). 1H NMR (DMSO-d6) δ 8.24 (d, J=8.7 Hz, 1H) 7.28-7.78 (m, 6H) 6.69 (d, J=1.7 Hz, 1H) 3.49 (s, 3H) 1.97 (s, 3H); MS calcd. for C18H14ClNO3 [(M+H)+] 328.0, obsd. 327.9.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe reaction mixture was filtered through a sintered glass funnel
  3. washthe solids were washed with MeOH (2×50 mL)
  4. concentrationThe combined filtrates were concentrated under reduced pressure
  5. customThe residue obtained
  6. washwashed with water (2×200 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified
  10. washby washing with a mixture of hexane-ether

출처 및 근거

ORD 기록
ord-e3239fa503fb4461853e99056f3d58b5
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501732B2

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