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

HRID 1350134ノート

反応式

HRID 1350134 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cc7dee57584c4864a91dd7e9601a2bb8
出典データセット
uspto-grants-2007_05
特許番号
US07214690B2

反応ノート

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