Water → HCID 66610575, compound

HRID 384971

Reaction equation

HRID 384971 reaction equation
[C@H:1]1([NH:10][CH:11]=[CH:12][CH:13]=[C:14]([C:19]([O:21]C)=[O:20])[C:15](OC)=[O:16])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[H-].[Na+].O>CO>[C@H:1]1([N:10]2[CH:11]=[CH:12][CH:13]=[C:14]([C:19]([OH:21])=[O:20])[C:15]2=[O:16])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 86649726(R)-dimethyl 2-(3-(2,3-dihydro-1H-inden-1-ylamino)allylidene)malonate

Product 1

HCID 66610575HCID 66610575, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 11.0 g (1.0 eq) (R)-dimethyl 2-(3-(2,3-dihydro-1H-inden-1-ylamino)allylidene)malonate in 80 ml dry MeOH was slowly added 3.65 g (2.5 eq) NaH (60% dispersion in mineral oil) under N2 protection. The reaction was stirred at room temperature for 10 minutes and was then heated at 60° C. After 20 minutes, to the reaction mixture were added 30 ml water. The resulting mixture was heated at 60° C. for an additional 20 minutes. The solvent was removed in vacuo. The residue was diluted with 50 ml water, and extracted with hexane (2×50 ml) to remove mineral oil. Then the aqueous mixture was acidified with 2N HCl to pH 1-2 and extracted with ethyl acetate (2×100 ml). The combined organic phase was washed with 100 ml brine, dried over sodium sulfate and concentrated in vacuo to afford (R)-1-(2,3-dihydro-1H-inden-1-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid as a white solid (8.7 g, yield 93%) which was used without further purification.

Workup

  1. temperaturewas then heated at 60° C
  2. waitAfter 20 minutes
  3. temperatureThe resulting mixture was heated at 60° C. for an additional 20 minutes
  4. customThe solvent was removed in vacuo
  5. additionThe residue was diluted with 50 ml water
  6. extractionextracted with hexane (2×50 ml)
  7. customto remove mineral oil
  8. extractionextracted with ethyl acetate (2×100 ml)
  9. washThe combined organic phase was washed with 100 ml brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-543b552766514cec86e03f43336154ea
Source dataset
uspto-grants-2013_02
Patent number
US08367836B2

Linked notes

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