Glutaric anhydride → HCID 21069606, 화합물

HRID 1371234노트

반응식

HRID 1371234 반응식
[NH2:1][C:2]1[C:7]([N:8]=[N:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=[C:4]([NH2:16])[N:3]=1.[C:17]1(=[O:24])[O:23][C:21](=[O:22])[CH2:20][CH2:19][CH2:18]1>O1CCCC1>[NH2:1][C:2]1[N:3]=[C:4]([NH:16][C:17](=[O:24])[CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH:5]=[CH:6][C:7]=1[N:8]=[N:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1

참가 물질

4

반응물 2

HCID 7940Glutaric anhydrideHCID 219095552,6-Diamino-3-((pyridin-3-yl)AZO)pyridine

생성물 1

HCID 21069606HCID 21069606, 화합물수율 40%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of 3.21 g (15 mmol) of 2,6-diamino-3-((pyridin-3-yl)azo)pyridine and 0.27 g (2.2 mmol) of N,N-dimethylamino-pyridine in 100 ml of tetrahydrofurane, 4.27 g (37.5 mmol) of glutaric anhydride was added at room temperature. The mixture was refluxed for 16 hours. The mixture was then filtered, the solvent was evaporated and the crude product was dissolved in ethylacetate and extracted three times with a 1N sodium hydroxide solution. The combined aqueous extracts were acidified with conc. HCI at 0° C. A precipitate was formed, and filtration yielded an orange solid. The solid so obtained was washed with water. After drying the product was recristallised in methanol/water mixture and 1.9 g (40% yield) of 5-[(6-amino-5-(3-pyridinyldiazenyl)-2-pyridinyl)amino]-5-oxopentanoic acid were obtained.

후처리

  1. additionwas added at room temperature
  2. temperatureThe mixture was refluxed for 16 hours
  3. filtrationThe mixture was then filtered
  4. customthe solvent was evaporated
  5. dissolutionthe crude product was dissolved in ethylacetate
  6. extractionextracted three times with a 1N sodium hydroxide solution
  7. customwere acidified with conc. HCI at 0° C
  8. customA precipitate was formed
  9. filtrationfiltration
  10. customyielded an orange solid
  11. customThe solid so obtained
  12. washwas washed with water
  13. customAfter drying the product

출처 및 근거

ORD 기록
ord-f14ce59befc345c79ca1c4c6f64cea7a
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07156884B2

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