Citric Acid → 4-Ethoxy-3-nitro-N-phenylbenzamide

HRID 1859652Notes

Reaction equation

HRID 1859652 reaction equation
F[C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:7])=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].[Na].C(O)(=O)[CH2:22][C:23](CC(O)=O)(C(O)=O)[OH:24]>C(O)C>[N+:17]([C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:2]=1[O:24][CH2:23][CH3:22])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7])([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 5360545SodiumHCID 18626075HCID 18626075, compound

Product 1

HCID 186261594-Ethoxy-3-nitro-N-phenylbenzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Fluoro-3-nitro-N-phenyl-benzamide from Example 9 (2.34 g, 9 mmol) was added all at once to a solution prepared by dissolving sodium metal (2.29 g, 100 mmol) in ethanol (100 mL). The reaction mixture was stirred 1 hour at room temperature, then citric acid solution (10% aqueous, 4 mL) was added, and the mixture allowed to stand overnight. The reaction mixture was then concentrated to dryness and the residue chromatographed on silica gel using hexane/ethyl acetate, 1:1, as eluant to afford the product as an orange solid (1.09 g); m.p. 189-190° C.

Workup

  1. customprepared
  2. waitto stand overnight
  3. concentrationThe reaction mixture was then concentrated to dryness
  4. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-0977f581a0de4e2787fb8970ce6f1fa3
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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