Toluene → HCID 178469351, 화합물

HRID 507937

반응식

HRID 507937 반응식
[Na].[C:2]([O:12][CH2:13][CH3:14])(=[O:11])[CH2:3][C:4]([C:6]([O:8]CC)=O)=O.C1(C)C=CC=CC=1.Cl.[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[NH:30][NH2:31]>C(O)(=O)C>[OH:8][C:6]1[N:30]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[CH3:23])[N:31]=[C:3]([C:2]([O:12][CH2:13][CH3:14])=[O:11])[CH:4]=1

참가 물질

5

반응물 3

HCID 1140TolueneHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 57351814Diethyl 2-oxosuccinate,sodium salt

생성물 1

HCID 178469351HCID 178469351, 화합물수율 22%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

To a mixture of diethyl oxalacetate sodium salt (10.5 g, 50 mmol), acetic acid (100 mL) and toluene (50 mL) was added an aqueous solution (50 mL) of (2-methylphenyl)hydrazine hydrochloride (7.93 g, 50 mmol) under stirring at room temperature, and the mixture was heated under reflux for 3 hr. After cooling, the reaction mixture was partitioned. The organic layer was washed with water and saturated brine, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-3/1) to give yellow crystals. This product was dissolved in acetic acid (36 mL), and the mixture was heated under reflux for 2 hr. After cooling, the reaction mixture was concentrated under reduced pressure, and recrystallized from hexane-ethyl acetate to give the title compound (2.69 g, yield 22%) as colorless crystals.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. temperatureAfter cooling
  4. customthe reaction mixture was partitioned
  5. washThe organic layer was washed with water and saturated brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-3/1)
  9. customto give yellow crystals
  10. temperaturethe mixture was heated
  11. temperatureunder reflux for 2 hr
  12. temperatureAfter cooling
  13. concentrationthe reaction mixture was concentrated under reduced pressure
  14. customrecrystallized from hexane-ethyl acetate

출처 및 근거

ORD 기록
ord-fe755205ce944513b949e8d98f2dc66a
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786165B2

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