3-Aminobenzoic Acid → HCID 178479313, compound

HRID 378126

Reaction equation

HRID 378126 reaction equation
[ClH:1].[C:2](=[NH:12])(OCC)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[NH2:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([OH:28])=[O:27]>O.O1CCOCC1>[ClH:1].[C:26]([C:25]1[CH:24]=[C:23]([NH:22][C:2](=[NH:12])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:31]=[CH:30][CH:29]=1)([OH:28])=[O:27]

Participants

6

Reactant 3

HCID 74193-Aminobenzoic AcidHCID 79249Benzenecarboximidic acid, ethyl ester, hydrochloride (1:1)HCID 81531Diisopropylethylamine

Product 1

HCID 178479313HCID 178479313, compoundYield 15.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To ethyl benzimidate hydrochloride (3 g, 0.016 mole)(Fluka) and (2.1 g, 0.016 mole) diisopropylethylamine in H2O (15 ml) and dioxane (15 ml) was added 3-aminobenzoic acid (2.22 g, 0.016 mole) (Aldrich). The reaction mixture was stirred at room temperature for 4 days. The resulting precipitate was filtered, washed with dioxane/H2O and dried. The precipitate was slurried in H2O and acidified with concentrated HCl. The solvent was removed under vacuum and the residue was slurried in ether. The ether was decanted off and the residue dried under vacuum to yield N-(3-carboxyphenyl)benzamidine hydrochloride (700 mg) as a white solid. MS and NMR were consistent with the desired structure.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with dioxane/H2O
  3. customdried
  4. customThe solvent was removed under vacuum
  5. customThe ether was decanted off
  6. customthe residue dried under vacuum

Sources & evidence

ORD record
ord-20ecb093fda34faba4686369b6b1f19d
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Linked notes

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