Hydrochloric Acid → HCID 25156888, compound

HRID 1019756Notes

Reaction equation

HRID 1019756 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([O:13][CH3:14])=[CH:6][C:5]=1F.[C:16]([O:23][CH3:24])(=[O:22])[CH2:17][C:18]([O:20][CH3:21])=[O:19].Cl>CN1CCCC1=O.O>[Cl:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([O:13][CH3:14])=[CH:6][C:5]=1[CH:17]([C:16]([O:23][CH3:24])=[O:22])[C:18]([O:20][CH3:21])=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7943Dimethyl malonateHCID 14798Sodium HydroxideHCID 534032891-Chloro-2-fluoro-4-methoxy-5-nitrobenzene

Product 1

HCID 25156888HCID 25156888, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydroxide (4.49 g, 112.3 mmol) was added at room temperature to a stirred solution of 1-chloro-2-fluoro-4-methoxy-5-nitrobenzene (11.0 g, 53.5 mmol) and dimethyl malonate (8.976 g, 67.9 mmol) in N-methylpyrrolidinone (110 mL). The mixture was heated to 80° C. for 2 hours then cooled to 5° C. The pH of the mixture was adjusted to 2 using aq. 1N HCl solution then water (600 mL) was added gradually with stirring over 15 minute at 5° C. The precipitated solid was collected by filtration and washed with water (2×20 mL). The filtered solid was dissolved in dichloromethane (150 mL), dried (Na2SO4) and concentrated under reduced pressure to give the title compound (15.5 g, 91%).

Workup

  1. temperaturethen cooled to 5° C
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water (2×20 mL)
  4. dissolutionThe filtered solid was dissolved in dichloromethane (150 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3fe833d354074cb7a6f69af28baec87b
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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