Hydrochloric Acid → HCID 16731996, compound

HRID 132683Notes

Reaction equation

HRID 132683 reaction equation
[Cl:1][C:2]1[C:3]([CH3:21])=[C:4]([CH:10](C(OCC)=O)[C:11]([O:13]CC)=[O:12])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[OH-].[Na+].CCOC(C)=O.Cl>CO>[Cl:1][C:2]1[C:3]([CH3:21])=[C:4]([CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 59734601Diethyl 2-(3-chloro-4-cyano-2-methylphenyl)malonate

Product 1

HCID 16731996HCID 16731996, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To compound 1F (2.3 g, 7.4 mmol) in 20 mL of MeOH was added 1N NaOH solution (30 mL, 30 mmol), and stirred at RT for 5 hr. It was concentracted, EtOAc was added, then acidified with conc. HCl. The biphase solution was heated at 60° C. for 2 hr, and cooled to RT. The organic layer was separated, dried over Na2SO4, filtered and concentrated to give the title compound (1.44 g). MS (ES) m/z 164 [M-CO2H]−.

Workup

  1. temperatureThe biphase solution was heated at 60° C. for 2 hr
  2. temperaturecooled to RT
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cbc7af0a31484382955b496236343866
Source dataset
uspto-grants-2008_06
Patent number
US07388027B2

Reaction notes

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