Dimethylformamide → Anthranilic Acid

HRID 375904Notes

Reaction equation

HRID 375904 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>CC([O-])=O.CC([O-])=O.[Cu+2].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

8

Reactant 4

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

Product 1

HCID 227Anthranilic Acid

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 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 (10mL) was refluxed for 4 hours and then was cooled to room temperature and was allowed to stand for about 3 days. Water was added to the reaction mixture and then the solution was acidified with acetic acid to a pH of about 5. The mixture was extracted with CH2Cl2 and then the CH2Cl2 layer was evaporated to afford N-(1-ethylpyrazol-5-yl)-5- trifluoromethylsulfonyl)anthranilic acid.

Workup

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

Sources & evidence

ORD record
ord-4bb2af8320624fd9b0ba0fc9dd0bbce4
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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