Acetic Acid → HCID 86757257, compound

HRID 650912Notes

Reaction equation

HRID 650912 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([NH:16]N)=[C:7]2[C:11]=1[C:10](=[O:12])[N:9]([CH:13]([CH3:15])[CH3:14])[CH2:8]2.CO.S(=O)(=O)(O)O.[OH-].[Na+].[CH3:27][C:28](O)=O>>[NH:9]1[CH2:8][CH2:7][CH2:6][NH:16][C:28]1=[CH:27][NH:16][C:6]1[CH:5]=[CH:4][C:3]([Cl:2])=[C:11]2[C:7]=1[CH2:8][N:9]([CH:13]([CH3:15])[CH3:14])[C:10]2=[O:12]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 21710146HCID 21710146, compound

Product 1

HCID 86757257HCID 86757257, compound

Procedure

A stirred solution of 4.3 grams (0.016 mole) of [7-chloro-2-(1-methylethyl)isoindolin-1-on-4-yl]hydrazine hydrochloride and 10 mL of methanol in 40 mL of HOAc was cooled in an ice-water bath and 2.6 grams (0/023 mole) of O-methylvalerolactin was added dropwise, followed by 0.5 gram (catalyst) of concentrated sulfuric acid. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature where it stirred for about 18 hours. After this time the reaction mixture was cooled, cold aqueous 10% sodium hydroxide was added, and the mixture was extracted with EtOAc. The combined extracts were washed with water, then with aqueous concentrated sodium chloride solution. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel using mixtures of EtOAc, hexane, and methanol as eluants. The fractions containing product were combined and concentrated under reduced pressure, yielding 1.4 grams of subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. addition2.6 grams (0/023 mole) of O-methylvalerolactin was added dropwise
  2. additionUpon completion of addition
  3. temperatureAfter this time the reaction mixture was cooled
  4. extractionthe mixture was extracted with EtOAc
  5. washThe combined extracts were washed with water
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure to a residue
  9. customThe residue was purified by column chromatography on silica gel using mixtures of EtOAc, hexane, and methanol as eluants
  10. additionThe fractions containing product
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-13725a3bb7184210aeb71424f84e0c79
Source dataset
uspto-grants-2001_08
Patent number
US06277847B1

Reaction notes

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