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

HRID 1244017Notes

Reaction equation

HRID 1244017 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0bddb941c2de4661b108a2513d5e972a
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

Loading…