Benzoic acid, 3-amino-, methyl ester → HCID 178497936, compound

HRID 1451065Notes

Reaction equation

HRID 1451065 reaction equation
[N-:1]([C:4]#[N:5])[C:2]#[N:3].[Na+].[NH2:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12]>O.Cl>[NH2:3][C:2]([NH:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])=[N:1][C:4]#[N:5]

Participants

5

Reactant 2

HCID 78274Benzoic acid, 3-amino-, methyl esterHCID 4350929Sodium dicyanamide

Product 1

HCID 178497936HCID 178497936, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To sodium dicyanamide in 5 mL of deionized water was added dropwise a solution of methyl 3-aminobenzoate (Aldrich, 1.30 g, 8.6 mmol) in 15 mL of 1N HCl. The resulting clear solution was heated at 80°-90° C. for 2 h. The precipitate was collected through filtration, crystallized from chloroform-methanol, dried in air followed by drying in a pistol at acetone reflux in vacuo to give 1.84 g (quantitative) of methyl 3-[amino(cyanoiminomethyl)]aminobenzoate as a white solid, mp 203°-204° C.

Workup

  1. temperatureThe resulting clear solution was heated at 80°-90° C. for 2 h
  2. filtrationThe precipitate was collected through filtration
  3. customcrystallized from chloroform-methanol
  4. customdried in air
  5. dry with materialby drying in a pistol at acetone
  6. temperaturereflux in vacuo

Sources & evidence

ORD record
ord-4f94aa49513249089a34d4cada52186b
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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