Methyl iodide → 8-fluoro-1-methyl-6-nitro-3,4-dihydro-1H-quinolin-2-one

HRID 1991324Notes

Reaction equation

HRID 1991324 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.I[CH3:17]>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[CH:5]=[C:6]2[C:11]=1[N:10]([CH3:17])[C:9](=[O:12])[CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 21877762HCID 21877762, compound

Product 1

HCID 218779148-fluoro-1-methyl-6-nitro-3,4-dihydro-1H-quinolin-2-oneYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

8-Fluoro-6-nitro-3,4-dihydro-1H-quinolin-2-one (Step 1, 3.13 g, 0.0149 mol) and iodomethane (1.39 ml, 0.0223 mol) in DMF (25 ml) are stirred at room temperature overnight. The reaction is diluted with water and the resulting precipitate collected by filtration, washed well with water, and dried under vacuum to give the title compound as an orange solid (2.97 g, 89%); 1H NMR (300 MHz, CDCl3) δ 2.56-2.61 (m, 2H), 2.99-3.04 (m, 2H), 3.32 (s, 3H), overlapping 8.06 (s, 1H) and 8.08 (dd, 1H); [M+H]+=225.

Workup

  1. filtrationthe resulting precipitate collected by filtration
  2. washwashed well with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-f70a806d72374d16a5c84be92bb878ba
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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