Water → HCID 53897108, compound

HRID 2187061Notes

Reaction equation

HRID 2187061 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].CC(C)([O-])C.[K+].F[C:19]1[CH:20]=[CH:21][C:22]([N+:29]([O-:31])=[O:30])=[C:23]([CH:28]=1)[C:24]([O:26][CH3:27])=[O:25].O>CN(C)C=O.Cl>[CH3:27][O:26][C:24]([C:23]1[CH:28]=[C:19]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])[CH:20]=[CH:21][C:22]=1[N+:29]([O-:31])=[O:30])=[O:25]

Participants

7

Reactant 4

HCID 962WaterHCID 7761Diethyl MalonateHCID 51520495-Fluoro-2-nitrobenzoic acid methyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 53897108HCID 53897108, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of diethyl malonate (8.04 ml, 52.9 mmol) in N,N-dimethylformamide (30.0 ml), potassium tert-butoxide (5.94 g, 52.9 mmol) was added, and, after complete dissolution, methyl 5-fluoro-2-nitrobenzoate (4.69 g, 26.5 mmol) obtained in Reference Example 107 was added. The reaction mixture was stirred at 60° C. for 25 hours and poured onto an iced water, made acidic with iN hydrochloric acid, and then extracted with ethyl acetate. After the extract was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure to give the title compound as an oil. This product was used in the next reaction without further purification.

Workup

  1. customobtained in Reference Example 107
  2. additionwas added
  3. extractionextracted with ethyl acetate
  4. washAfter the extract was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-845e2440468f4091b62cc4eebd611b40
Source dataset
uspto-grants-2002_06
Patent number
US06407116B1

Reaction notes

Loading…