Sodium Chloride → HCID 57940692, compound

HRID 1437217Notes

Reaction equation

HRID 1437217 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH3:13])=[N:10][CH:11]=1.[Cl-].[Na+].O.O.[Sn](Cl)Cl.[CH2:21]([O:23][C:24](=[O:37])[C:25](=O)[CH:26]1[CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]1=O)[CH3:22].[OH-].[Na+]>O.Cl.C(O)C>[CH2:21]([O:23][C:24]([C:25]1[C:26]2[CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]=2[N:5]([C:6]2[CH:11]=[N:10][C:9]([CH2:12][CH3:13])=[CH:8][CH:7]=2)[N:1]=1)=[O:37])[CH3:22]

Participants

10

Reactant 6

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 138607296-Ethylpyridin-3-amineHCID 15073465HCID 15073465, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 57940692HCID 57940692, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium nitrite (228 mg) in water (1 mL) was added dropwise to 5-amino-2-ethylpyridine (359 mg) in concentrated hydrochloric acid (3 mL) under cooling with ice with sodium chloride over a period of 10 minutes, followed by stirring at a constant temperature for 10 minutes. Tin(II) chloride dihydrate (2.37 g) in concentrated hydrochloric acid (1.6 mL) was added dropwise to the reaction mixture over a period of 10 minutes, followed by stirring with ice cooling for 3 hours. 2-Oxo-2-(1-oxoindan-2-yl)acetic acid ethyl ester (696 mg) obtained from Referential Example 62 in ethanol (20 mL) was added to the reaction mixture. The resultant mixture was refluxed under heat for 39 hours. Under cooling with ice, the reaction mixture was alkalinized by use of an aqueous solution of sodium hydroxide. The resultant mixture was partitioned between ethyl acetate and water. The organic layer was sequentially washed with water and saturated brine, and then dried over sodium sulfate anhydrate. Subsequently, the mixture was subjected to filtration. The solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform-acetone), to thereby give the title compound as crystals (372 mg, 37%).

Workup

  1. stirringby stirring with ice cooling for 3 hours
  2. additionwas added to the reaction mixture
  3. temperatureunder heat for 39 hours
  4. temperatureUnder cooling with ice
  5. customThe resultant mixture was partitioned between ethyl acetate and water
  6. washThe organic layer was sequentially washed with water and saturated brine
  7. dry with materialdried over sodium sulfate anhydrate
  8. filtrationSubsequently, the mixture was subjected to filtration
  9. customThe solvent was evaporated under reduced pressure
  10. customThe residue was purified through silica gel column chromatography (chloroform-acetone)

Sources & evidence

ORD record
ord-e9bc19880915411eb7e67952c0d56f08
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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