6-Methoxy-1-methyl-3,4-dihydroquinolin-2(1H)-one → 6-Hydroxy-1-methyl-3,4-dihydroquinolin-2(1H)-one

HRID 1244017ノート

反応式

HRID 1244017 の反応式
B(Br)(Br)Br.C(Cl)Cl.C[O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[C:15](=[O:21])[CH2:14][CH2:13]2>C(Cl)Cl>[OH:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[C:15](=[O:21])[CH2:14][CH2:13]2

参加物

4

反応物 2

HCID 107977876-Methoxy-1-methyl-3,4-dihydroquinolin-2(1H)-oneHCID 22277759Boron tribromide dichloromethane

生成物 1

HCID 219318286-Hydroxy-1-methyl-3,4-dihydroquinolin-2(1H)-one収率 84.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

5.74 ml of 1.0 M BBr3/CH2Cl2 solution was added to a dry CH2Cl2 solution of 6-methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one (500 mg, 2.62 mmol) under nitrogen. The reaction mixture was stirred for 2 hours, poured into ice water and extracted with ethyl acetate (150 ml). The combined organic extract was washed with brine,dried (MgSO4) and the solvent was evaporated under reduced pressure to yield the title compound as a pink solid (392 mg, 84%). 1H NMR (400 MHz, CD3OD) δ 2.52–2.56 (2H, m), 2.77–2.81 (2H, m), 3.28 (3H, s), 6.62–6.67 (2H, m), 6.92 (1H, d, J=8.72 Hz). m/z (APCI−) 176 (M−1). HPLC (aqueous 200 Mm ammonium acetate buffer/acetonitrile gradient, 3.0 ml/min, Hewlett Packard ODS Hypersil 5 μM, 125×4 mm column), 2.51 minutes.

後処理

  1. extractionextracted with ethyl acetate (150 ml)
  2. extractionThe combined organic extract
  3. washwas washed with brine,dried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-0bddb941c2de4661b108a2513d5e972a
出典データセット
uspto-grants-2006_10
特許番号
US07119207B2

反応ノート

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