Succinic anhydride → HCID 22997463, compound

HRID 1166163Notes

Reaction equation

HRID 1166163 reaction equation
[CH2:1]([C:3]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[N:9]([C:13]([CH3:18])=[C:14]([CH2:16][OH:17])[N:15]=2)[CH:10]=[CH:11][CH:12]=1)[CH3:2].[H-].[Na+].[C:26]1(=[O:32])[O:31][C:29](=[O:30])[CH2:28][CH2:27]1>C(#N)C>[CH2:1]([C:3]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[N:9]([C:13]([CH3:18])=[C:14]([CH2:16][O:17][C:26](=[O:32])[CH2:27][CH2:28][C:29]([OH:31])=[O:30])[N:15]=2)[CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 24758Sodium hydrideHCID 9818119HCID 9818119, compound

Product 1

HCID 22997463HCID 22997463, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 8-(2-ethyl-6-methylbenzylamino)-2-hydroxymethyl-3-methylimidazo[1,2-a]pyridine (0.47 g, 1.5 mmol) in acetonitrile (20 ml) was added sodium hydride (50% in oil) (0.081 g, 1.7 mmol) and the mixture was stirred for 5 min. To the mixture was added succinic anhydride (0.23 g, 2.3 mmol) and the reaction mixture was refluxed for 20 h. The solvent was evaporated under reduced pressure. The residue was suspended in water and the pH was adjusted to 6 with 2M HCl and the solid that formed was isolated by centrifuging. Washing with water and with acetonitrile gave 0.51 g, (82%) of the desired product.

Workup

  1. temperaturethe reaction mixture was refluxed for 20 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe solid that formed
  4. customwas isolated by centrifuging
  5. washWashing with water and with acetonitrile

Sources & evidence

ORD record
ord-0bf81562ec1c4572a9cec89f736e6ce2
Source dataset
uspto-grants-2003_09
Patent number
US06613775B1

Reaction notes

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