Hydrochloric Acid → HCID 59645465, compound

HRID 2253311Notes

Reaction equation

HRID 2253311 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8](Cl)[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:16]([O:24][CH2:25][CH3:26])(=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C>[NH2:1][C:2]1[C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:8]([CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:16]([O:24][CH2:25][CH3:26])=[O:23])[CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 11430Potassium CarbonateHCID 59645472methyl 2-amino-6-chloro-3-nitrobenzoate

Product 1

HCID 59645465HCID 59645465, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 2-amino-6-chloro-3-nitrobenzoate (4.11 g, 17.8 mmol), diethyl malonate (4.85 g, 30.3 mmol) and solid K2CO3 (powder, 9.11 g, 65.9 mmol) in DMF (71 mL) was heated at 60° C. for 10 h. The reaction mixture was poured into aqueous 1N HCl solution (400 mL) and the resulting solution was extracted with EtOAc (2×250 mL). The combined organic layers were washed with water (3×150 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated under reduced pressure. Purification by flash chromatography (10-40μ silica gel; hexane:EtOAc 3:1) provided the title compound (4.80 g, 76% yield) as a yellow solid.

Workup

  1. extractionthe resulting solution was extracted with EtOAc (2×250 mL)
  2. washThe combined organic layers were washed with water (3×150 mL) and brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography (10-40μ silica gel; hexane:EtOAc 3:1)

Sources & evidence

ORD record
ord-df4076e05c73430bb0b6b8b8d3a2b886
Source dataset
uspto-grants-2008_01
Patent number
US07323567B2

Reaction notes

Loading…