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

HRID 1244017노트

반응식

HRID 1244017 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0bddb941c2de4661b108a2513d5e972a
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119207B2

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