Hydrochloric Acid → 4-[2-(2-Nitrobenzoylamino)benzoylamino]butanoic acid

HRID 2374708Notes

Reaction equation

HRID 2374708 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:5].[N+:17]([C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23])([O-:19])=[O:18].[OH-].[Na+].Cl>C(OCC)(=O)C.C(N(CC)CC)C>[N+:17]([C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([NH:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:5])=[O:23])([O-:19])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 118752-Nitrobenzoyl chlorideHCID 14798Sodium HydroxideHCID 134423754-(2-Aminobenzamido)butanoic acid

Product 1

HCID 231185564-[2-(2-Nitrobenzoylamino)benzoylamino]butanoic acid

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of 3.90 g (17.50 mmol) of 4-(2-aminobenzoylamino)butanoic acid in 40 ml of dry ethyl acetate, add 3.26 g (17.56 mmol) of 2-nitrobenzoyl chloride dissolved in 5 ml of dry ethyl acetate and 1.76 g of triethylamine. Allow the reaction mixture to stir for 24 hours at room temperature. Eliminate the solvent at low pressure, add 30 ml of 10% NaOH to the crude product and continue stirring the mixture until the solid has completely disappeared. Immediately acidify with concentrated HCl and extract the product with ethyl acetate. Eliminate the solvent at low pressure and recombine the crude product with dry ether, obtaining a white solid. Purify the reaction product by recrystallization (EtOH/H2O). This yields 3.34 g (51%) of 4-[2-(2-nitrobenzoylamino)benzoylamino]butanoic acid as a white solid.

Workup

  1. stirringcontinue stirring the mixture until the solid
  2. extractionextract the product with ethyl acetate
  3. customobtaining a white solid
  4. customPurify the reaction product
  5. customby recrystallization (EtOH/H2O)

Sources & evidence

ORD record
ord-72041cb47dfe415d8cde2bb5502f23da
Source dataset
uspto-grants-2008_12
Patent number
US07462735B2

Reaction notes

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