Methyl iodide → 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-1-methyl-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1857647Notes

Reaction equation

HRID 1857647 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([N+:27]([O-:29])=[O:28])[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:43]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([N+:27]([O-:29])=[O:28])[CH:25]=2)[N:20]([CH3:43])[C:19](=[O:31])[C:18]=1[C:32]1[CH:33]=[C:34]([CH3:39])[CH:35]=[C:36]([CH3:38])[CH:37]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 543943462-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 537246792-{2-[7-Chloro-3-(3,5-dimethylphenyl)-1-methyl-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Procedure

To a solution of 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (100 mg in 3.5 mL N,N-dimethylformamide) at 0° C. was added 7.6 mg sodium hydride and the mixture stirred for 1 hour at low temperature. At this time, 0.012 mL iodomethane were added continued stirring. After 30 minutes, the reaction was quenched by the addition of saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic portion was washed with water and brine then dried over magnesium sulfate to give the crude title compound.

Workup

  1. stirringcontinued stirring
  2. waitAfter 30 minutes
  3. customthe reaction was quenched by the addition of saturated aqueous ammonium chloride
  4. extractionextracted with ethyl acetate
  5. washThe organic portion was washed with water and brine
  6. dry with materialthen dried over magnesium sulfate

Sources & evidence

ORD record
ord-408c74cfcd4e4e61af7deef8499ef2a7
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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