HCID 86683907, compound → HCID 67468383, compound

HRID 2405009Notes

Reaction equation

HRID 2405009 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18](C(OCC)=O)[C:19]([O:21]CC)=[O:20])[C:13]1=[O:29]>O.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][C:19]([OH:21])=[O:20])[C:13]1=[O:29]

Participants

4

Reactant 1

HCID 86683907HCID 86683907, compound

Product 1

HCID 67468383HCID 67468383, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
45 °C

Procedure

The crude product solution of diethyl [1-(2-methoxy-4-nitrophenyl)-2-oxo-1,2-dihydropyridin-3-yl]malonate (maximum 0.12 mol) was diluted with 390 ml of water, and 39 ml of concentrated sodium hydroxide solution were slowly added. The reaction mixture was stirred at 45° C. for 90 min, cooled to RT, diluted with water and extracted three times with dichloromethane. The organic phase was discarded, and the aqueous phase was admixed with 300 ml of dichloromethane and adjusted to pH 1 at 15° C. with concentrated hydrochloric acid. Even in a weakly acidic medium, the evolution of carbon dioxide arises. After warming to RT, stirring was carried out for 1 h, then the phases were separated and the organic phase was dried over sodium sulphate, filtered and concentrated to dryness on a rotary evaporator. The residue was stirred with acetonitrile, filtered with suction, after-washed and dried in vacuo. This gave 17.4 g (49%) of the desired compound. The mother liquor was evaporated to dryness, stirred with acetonitrile and worked-up analogously. This gave a further 3.6 g (10%) of the desired compound.

Workup

  1. additionwere slowly added
  2. temperaturecooled to RT
  3. extractionextracted three times with dichloromethane
  4. customadjusted to pH 1 at 15° C. with concentrated hydrochloric acid
  5. temperatureAfter warming to RT
  6. stirringstirring
  7. waitwas carried out for 1 h
  8. customthe phases were separated
  9. dry with materialthe organic phase was dried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated to dryness on a rotary evaporator
  12. stirringThe residue was stirred with acetonitrile
  13. filtrationfiltered with suction
  14. washafter-washed
  15. customdried in vacuo
  16. customThe mother liquor was evaporated to dryness
  17. stirringstirred with acetonitrile

Sources & evidence

ORD record
ord-505c550f5de44be0a2d0f51bdeed4068
Source dataset
uspto-grants-2014_08
Patent number
US08802860B2

Reaction notes

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