Succinic anhydride → N-n-hexyl 5-(3-carboxy-propionyloxy)-2-hydroxybenzamide

HRID 1969163Notes

Reaction equation

HRID 1969163 reaction equation
[CH2:1]([NH:7][C:8](=[O:17])[C:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=1[OH:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:18]1(=[O:24])[O:23][C:21](=[O:22])[CH2:20][CH2:19]1>C(Cl)Cl>[CH2:1]([NH:7][C:8](=[O:17])[C:9]1[CH:14]=[C:13]([O:15][C:18](=[O:24])[CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH:12]=[CH:11][C:10]=1[OH:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 69460565HCID 69460565, compound

Product 1

HCID 24873250N-n-hexyl 5-(3-carboxy-propionyloxy)-2-hydroxybenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-n-Hexyl 2,5-dihydroxybenzamide (1 g) is dissolved in 15 mL of methylene chloride. To the solution 0.75 g of succinic anhydride and 0.95 g of 4-N,N-dimethylaminopyridene is added. The reaction mixture is allowed to stir at ambient conditions over 24 hours. Solvent is removed and the residue is reconstituted in ethyl acetate and extracted twice with 1 N HCl to remove the catalyst. The organic layer is further extracted with saturated sodium chloride solution and dried over anhydrous sodium sulfate. Solvent is removed under reduced pressure to yield the product as an off-white powder.

Workup

  1. customSolvent is removed
  2. extractionextracted twice with 1 N HCl
  3. customto remove the catalyst
  4. extractionThe organic layer is further extracted with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customSolvent is removed under reduced pressure

Sources & evidence

ORD record
ord-8b2b85957fde42fdab09649c129cd721
Source dataset
uspto-grants-2013_04
Patent number
US08426466B2

Reaction notes

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