Hydrochloric Acid → 6-bromo-5-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one

HRID 1350134노트

반응식

HRID 1350134 반응식
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:13]([F:16])([F:15])[F:14])=[CH:5][C:6](=[O:12])[NH:7]2.C(NC(C)C)(C)C.[Br:24]N1C(=O)CCC1=O.Cl>CCOC(C)=O>[Br:24][C:11]1[C:2]([OH:1])=[C:3]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:12])[CH:5]=[C:4]2[C:13]([F:16])([F:14])[F:15]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 67184N-bromobutanimideHCID 210943825-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one

생성물 1

HCID 210943856-bromo-5-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one수율 77%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of 5-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one (4.38 g, 19.1 mmol) and diisopropylamine (14 mL, 100 mmol) in 100 mL EtOAc was added a solution of N-bromosuccinimide (3.74 g, 21.0 mmol) in 70 mL EtOAc at −10° C. over 30 min. The reaction mixture was stirred for 1 h, then acidified to pH 1 by the addition of 6M HCl. The mixture was extracted with EtOAc (3×150 mL) and the combined organic layers were washed with brine (200 mL), dried over MgSO4, filtered and concentrated under reduced pressure. Recrystallization from chloroform:hexanes afforded 4.5 g (77%) of 6-bromo-5-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one, an off-white solid. Rf0.4 (1:1 EtOAc:hexanes); 1H NMR (400 MHz, acetone-d6) δ 11.1 (broad s, 1H), 8.75 (broad s, 1H), 7.76 (d, 1H, J=8.8), 7.04 (d, 1H, J=8.8), 6.98 (s, 1H).

후처리

  1. extractionThe mixture was extracted with EtOAc (3×150 mL)
  2. washthe combined organic layers were washed with brine (200 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customRecrystallization from chloroform

출처 및 근거

ORD 기록
ord-cc7dee57584c4864a91dd7e9601a2bb8
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07214690B2

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