Hydrochloric Acid → Ethyl 4-(3-aminobenzamido)benzoate

HRID 2241126Notes

Reaction equation

HRID 2241126 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:22])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)=[CH:7][CH:6]=1)[CH3:2].[Sn].Cl>C1COCC1>[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:22])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=2)=[CH:9][CH:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 711477Benzoic acid, 4-[(3-nitrobenzoyl)amino]-, ethyl esterHCID 5352426Tin atom

Product 1

HCID 24271945Ethyl 4-(3-aminobenzamido)benzoateYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-(3-nitro-benzoylamino)-benzoic acid ethyl ester (0.50 g, 1.59 mmol) in THF (5.0 ml) was treated with tin metal (0.38 g, 3.18 mmol) and 6N HCl (2.5 ml). The mixture was warmed to 50° C. and stirred for 30 min. After cooling to room temperature, the solvent was evaporated, and the residue treated with 10% aqueous NaOH (10.0 ml). The resulting suspension was filtered, washing with water. The solid was dissolved in THF and treated with Na2SO4. After filtration, the filtrate was evaporated to yield 4-(3-amino-benzoylamino)-benzoic acid ethyl ester (0.36 g, 80%) as a light yellow solid, MS (ISP): m/e=285.3 (M+H+).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was evaporated
  3. additionthe residue treated with 10% aqueous NaOH (10.0 ml)
  4. filtrationThe resulting suspension was filtered
  5. washwashing with water
  6. dissolutionThe solid was dissolved in THF
  7. additiontreated with Na2SO4
  8. filtrationAfter filtration
  9. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-5908751e3ebc4d3a8e225e10be3832dc
Source dataset
uspto-grants-2010_05
Patent number
US07723538B2

Reaction notes

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