Dimethylformamide → Anthranilic Acid

HRID 1586188Notes

Reaction equation

HRID 1586188 reaction equation
N[C:2]1N(CC)[N:5]=[CH:4][CH:3]=1.Cl[C:10]1[CH:18]=CC(S(C(F)(F)F)(=O)=O)=C[C:11]=1[C:12]([OH:14])=[O:13].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>C(O)(=O)C.O>[C:12]([OH:14])(=[O:13])[C:11]1[C:4](=[CH:3][CH:2]=[CH:18][CH:10]=1)[NH2:5]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3373101-Ethyl-1H-pyrazol-5-amineHCID 21217711HCID 21217711, compound

Product 1

HCID 227Anthranilic Acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 5-amino-1-ethylpyrazole (0.56 g, 5 mmol), 2-chloro-5-(trifluoromethylsulfonyl)benzoic acid (1.4 g, 4.9 mmol), K2CO3 (0.69 g, 5 mmol), Cu(OAc)<2>(0.1 g) and DMF (10 ml) is refluxed for 4 hours and then is cooled to room temperature and is allowed to stand for about 3 days. Water is added to the reaction mixture, and then the solution is acidified with acetic acid to a pH of about 5. The mixture is extracted with CH2Cl2 and then the CH2Cl2 layer is evaporated to afford N-(1-ethylpyrazol-5-yl)-5-trifluoromethylsulfonyl)anthranilic acid.

Workup

  1. temperatureis refluxed for 4 hours
  2. extractionThe mixture is extracted with CH2Cl2
  3. customthe CH2Cl2 layer is evaporated

Sources & evidence

ORD record
ord-b5d969a5de6148d3869c98092a66e808
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

Loading…