Guanidine → 1,4-Naphthalenedicarboxylic acid

HRID 1359617Notes

Reaction equation

HRID 1359617 reaction equation
[C:1]1([C:15]([O:17]C)=[O:16])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([O:13]C)=[O:12])=[CH:3][CH:2]=1.NC(N)=N>C(O)(C)C>[C:1]1([C:15]([OH:17])=[O:16])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=[O:12])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 3520GuanidineHCID 11064621DIMETHYL 1,4-NAPHTHALENEDICARBOXYLATE

Product 1

HCID 690651,4-Naphthalenedicarboxylic acidYield 42.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1.2 g of dimethyl naphthaline-1,4-dicarboxylate and 3 g of guanidine are dissolved in 10 ml of anhydrous isopropanol and the solution is boiled under reflux for 4 h. The solvent is removed in vacuo, the residue is slurried with water and the product is filtered off. 450 mg of naphthaline-1,4-dicarboxylic acid diguanidide are obtained; m.p.: 270° C. (Decomposition); Rf (acetone/water 10:1)=0.14; MS (FAB):299 (M+H)+.

Workup

  1. temperatureunder reflux for 4 h
  2. customThe solvent is removed in vacuo
  3. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-df2482e2e17a435faef7c53848f00791
Source dataset
uspto-grants-2003_07
Patent number
US06600072B2

Reaction notes

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