Iodine → 7-Iodo-6-methoxy-1-methyl-3,4-dihydro-1h-quinolin-2-one

HRID 1244023Notes

Reaction equation

HRID 1244023 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[C:8](=[O:14])[CH2:7][CH2:6]2.[I:15]I>FC(F)(F)C([O-])=O.[Ag+].C(Cl)Cl>[I:15][C:12]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:14])[N:9]2[CH3:13])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 807IodineHCID 107977876-Methoxy-1-methyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 219317427-Iodo-6-methoxy-1-methyl-3,4-dihydro-1h-quinolin-2-oneYield 48%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Silver trifluoroacetate (2.32 g, 10.48 mmol) was added to a dry methylene chloride (100 ml) solution of 6-Methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one (1.0 g, 5.24 mmol) followed by the dropwise addition of methylene chloride (100 ml) solution of iodine (1.33 g, 10.48 mmol) over 15 minutes. The reaction mixture was stirred overnight and the precipitated silver iodide salts were filtered off. The filtrate was concentrated down to a residue which was chromatographed using 50% ethylacetate/hexane to yield the title compound (795 mg, 48% yield). 1H NMR (400 MHz, CDCl3) δ 2.57–2.61 (2H, m), 2.81–2.85 (2H, m), 3.27 (3H, s), 3.82 (3H, s), 6.62 (1H, s), 7.31 (1H, s). m/z (APCI+) 318 (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), 4.959 min.

Workup

  1. filtrationthe precipitated silver iodide salts were filtered off
  2. concentrationThe filtrate was concentrated down to a residue which
  3. customwas chromatographed

Sources & evidence

ORD record
ord-97e804b032474ed085e9864e322db833
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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