Sodium Carbonate → HCID 14474160, compound

HRID 482012Notes

Reaction equation

HRID 482012 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C([O-])([O-])=[O:14].[Na+].[Na+]>OS(O)(=O)=O>[NH2:1][C:2]1[CH:10]=[C:9]([C:11](=[O:14])[NH2:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 103519812-Amino-4-cyanobenzoic acid

Product 1

HCID 14474160HCID 14474160, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
45 °C

Procedure

2-amino-4Cyanobenzoic acid (3.01 g, 18.3 mmol), prepared by the method of Chan and Bruice, J. Am. Chem. Soc., 99: 6721 (1977), was dissolved in 60 mL of 97% H2SO4 and heated to 45° C. for 12 h. The mixture was added to ice, and saturated Na2CO3 solution was added to adjust the pH=3. The mixture was then filtered, and the yellow solid lyophilized to yield the title compound (2.94 g, 89%): mp 276°-278° C. 1H NMR (300 MHz, DMSO-d6) δ 8.72 (br s, 3H), 7.90 (br s, 1H), 7.71 (d, 1H), 7.37 (br s, 1H), 7.21 (d, 1H), 6.92 (dd, 1H), 6.75 (br s, 2H); MS (DCI/NH3) m/z 181 (M+H)+.

Workup

  1. additionwas added
  2. filtrationThe mixture was then filtered

Sources & evidence

ORD record
ord-3722a4093d5b4915b4ec382f54a18702
Source dataset
uspto-grants-1998_08
Patent number
US05792767

Reaction notes

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