Glutaric anhydride → HCID 86760494, compound

HRID 1354533Notes

Reaction equation

HRID 1354533 reaction equation
[NH2:1][C:2]1[CH:15]=[C:14]2[C:9]([N:10]=[CH:11][CH:12]=[CH:13]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:16]1(=[O:23])O[C:20](=[O:21])[CH2:19][CH2:18][CH2:17]1>N1C=CC=CC=1.C(N(CC)CC)C>[NH2:1][C:2]1[CH:15]=[C:14]2[C:9]([N:10]=[CH:11][CH:12]=[CH:13]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:16]1(=[O:23])[NH:1][C:20](=[O:21])[CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 7940Glutaric anhydrideHCID 6069701,10-Phenanthrolin-5-amine

Product 1

HCID 86760494HCID 86760494, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

5-Amino-1,10-phenanthroline (350 mg, 1.8 mmol) was refluxed with glutaric anhydride (2.0g, 17.5 mmol) in pyridine (3 mL) and triethylamine (3 mL) for 2 hours. The reaction mixture was reduced to a viscous oil by rotary evaporation. Column purification on silica with 10% methanol in methylene chloride (product produced bright red spots with Fe(II) on TLC) gave the crude product (320 mg 1.1 mmol). Further purification of the crude product was by recrystallization once from 30 mL boiling water to give the title compound (250 mg, 0.85 mmol) as centimeter long transparent needles.

Workup

  1. customThe reaction mixture was reduced to a viscous oil by rotary evaporation
  2. customColumn purification on silica with 10% methanol in methylene chloride (product produced bright red spots with Fe(II) on TLC)
  3. customgave the crude product (320 mg 1.1 mmol)
  4. customFurther purification of the crude product
  5. customwas by recrystallization once from 30 mL

Sources & evidence

ORD record
ord-cede7713117a4d83a5051002c2bd2dd7
Source dataset
uspto-grants-2007_05
Patent number
US07223833B1

Reaction notes

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