Glutaric anhydride → 5-[4-(3,5-Dioxohexyl)anilino]-5-oxopentanoic acid

HRID 2111518Notes

Reaction equation

HRID 2111518 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15])=[CH:6][CH:5]=1)([O-])=O.[O:18]1[C:23](=[O:24])[CH2:22][CH2:21][CH2:20][C:19]1=[O:25]>O1CCCC1>[O:17]=[C:12]([CH2:13][C:14](=[O:16])[CH3:15])[CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([NH:1][C:23]([CH2:22][CH2:21][CH2:20][C:19]([OH:25])=[O:18])=[O:24])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7940Glutaric anhydrideHCID 18717149HCID 18717149, compound

Product 1

HCID 187171485-[4-(3,5-Dioxohexyl)anilino]-5-oxopentanoic acidYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

200 mL tetrahydrofuran, 6-(4-nitro-phenyl)-hexane-2,4-dione (8.0 g, 34.0 mmol) and dihydro-pyran-2,6-dione (3.88 g, 34.0 mmol) were added to a reaction vessel. The reaction vessel was purged three times with argon. Approximately 200 mg palladium (10 wt % on activated carbon) was added. The reaction vessel was purged again with argon and excess hydrogen introduced via a balloon. Solution stirred 16 hours at room temperature. Hydrogen removed under reduced pressure and catalyst removed by filtration through celite. Tetrahydrofuran removed under reduced pressure to afford title compound (10.5 g, 97%, yellow solid).

Workup

  1. customThe reaction vessel was purged three times with argon
  2. additionApproximately 200 mg palladium (10 wt % on activated carbon) was added
  3. customThe reaction vessel was purged again with argon and excess hydrogen
  4. additionintroduced via a balloon
  5. customHydrogen removed under reduced pressure and catalyst
  6. customremoved by filtration through celite
  7. customTetrahydrofuran removed under reduced pressure

Sources & evidence

ORD record
ord-0a27f63d15de44fab695497e01d05afb
Source dataset
uspto-grants-2009_04
Patent number
US07521425B2

Reaction notes

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