Potassium Acetate → 5-amino-3,4-dihydro-4-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one

HRID 1350132노트

반응식

HRID 1350132 반응식
[NH2:1][C:2]1[CH:11]=[C:10](Cl)[CH:9]=[C:8]2[C:3]=1[C:4]([OH:18])([C:14]([F:17])([F:16])[F:15])[CH2:5][C:6](=[O:13])[NH:7]2.CC([O-])=O.[K+]>C(O)C.[Pd]>[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([OH:18])([C:14]([F:17])([F:15])[F:16])[CH2:5][C:6](=[O:13])[NH:7]2

참가 물질

5

반응물 2

HCID 517044Potassium AcetateHCID 222791795-amino-7-chloro-3,4-dihydro-4-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one

생성물 1

HCID 210943795-amino-3,4-dihydro-4-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one수율 101.5%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A mixture of 5-amino-7-chloro-3,4-dihydro-4-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one (8.0 g, 28 mmol), KOAc (5.6 g, 57 mmol) and 10% Pd—C (4.0 g) in 200 mL ethanol was stirred under an atmosphere of hydrogen for 2 h. The mixture was filtered through Celite and concentrated under reduced pressure. The resultant solid was dissolved in EtOAc (250 mL) and washed sequentially with saturated NaHCO3 (200 mL) and brine (200 mL), dried over MgSO4, filtered and concentrated to afford 7.0 g (100%) of 5-amino-3,4-dihydro-4-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one, a foamy tan solid. 1H NMR (400 MHz, acetone-d6) δ 9.16 (broad s, 1H), 6.99 (t, 1H, J=8.0), 6.44 (broad s, 1H), 6.39 (d, 1H, J=7.9), 6.26 (d, 1H, J=7.9), 5.44 (broad s, 2H), 3.09 (d, AB, J=17.0), 2.93 (d, AB, J=17.0).

후처리

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resultant solid was dissolved in EtOAc (250 mL)
  4. washwashed sequentially with saturated NaHCO3 (200 mL) and brine (200 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-140177cda5c342e59c274f1aebd6704f
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07214690B2

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