Dimethylformamide → N-(1,3-Dimethyl-5-pyrazolyl)anthranilic acid

HRID 1458744Notes

Reaction equation

HRID 1458744 reaction equation
I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:11][C:12]1[N:16]([CH3:17])[N:15]=[C:14]([CH3:18])[CH:13]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C>[CH3:17][N:16]1[C:12]([NH:11][C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:13][C:14]([CH3:18])=[N:15]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 69412-Iodobenzoic acidHCID 11430Potassium CarbonateHCID 5207211,3-Dimethyl-1H-pyrazol-5-amine

Product 1

HCID 615796N-(1,3-Dimethyl-5-pyrazolyl)anthranilic acidYield 44.7%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-iodobenzoic acid (14.9 g, 0.06 mol), 5-amino-1,3-dimethylpyrazole (6.7 g, 0.06 mol), DMF (125 ml), Cu(OAc)2 (0,4 g) and K2CO3 (8.28 g, 0.06 mol) is refluxed overnight. The reaction mixture is poured into ice water (500 ml) and then is acidified with acetic acid to a pH of about 5. The solid that forms is collected by filtration, washed with water (100 ml) and dried. The solid is dissolved in hot CHCl3 (300 ml), filtered, dried over MgSO4 and evaporated to about 20 ml. Hexane (50 ml) is added, and then the product is collected by filtration, washed with hexane (30 ml) and dried to afford 6.2 g of N-(1,3-dimethyl-pyrazol-5-yl)anthranilic acid, m.p. 210°-211° C.

Workup

  1. temperatureis refluxed overnight
  2. filtrationThe solid that forms is collected by filtration
  3. washwashed with water (100 ml)
  4. customdried
  5. dissolutionThe solid is dissolved in hot CHCl3 (300 ml)
  6. filtrationfiltered
  7. dry with materialdried over MgSO4
  8. customevaporated to about 20 ml
  9. additionHexane (50 ml) is added
  10. filtrationthe product is collected by filtration
  11. washwashed with hexane (30 ml)
  12. customdried

Sources & evidence

ORD record
ord-bd678c3d52f2435bb18b5326faa3499b
Source dataset
uspto-grants-1998_12
Patent number
US05852035

Reaction notes

Loading…