Glutaric anhydride → HCID 21069606, compound

HRID 1371234Notes

Reaction equation

HRID 1371234 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 21069606HCID 21069606, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f14ce59befc345c79ca1c4c6f64cea7a
Source dataset
uspto-grants-2007_01
Patent number
US07156884B2

Reaction notes

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