Dimethylformamide → N-(1-phenylmethylpyrazol-5-yl) anthranilic acid

HRID 1586142Notes

Reaction equation

HRID 1586142 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]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:15]=[CH:14][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.O>[C:18]1([CH2:17][N:16]2[C:12]([NH:11][C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]([OH:6])=[O:5])=[CH:13][CH:14]=[N:15]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 69412-Iodobenzoic acidHCID 11430Potassium CarbonateHCID 770611-Benzyl-1H-pyrazol-5-amine

Product 1

HCID 54572611N-(1-phenylmethylpyrazol-5-yl) anthranilic acid

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 2-iodobenzoic acid (14 g, 0.057 mol), 5-amino-1-phenylmethylpyrazole (9.8 g, 0.057 mol), DMF (140 ml), potassium carbonate (8.3 g) and Cu(OAc)2 (0.1 g) is refluxed for about 2 days. The reaction mixture is poured into water, acidified with acetic acid to a pH of 5, and then the solid which forms is collected by filtration, washed with water, then ether and then is dried to afford N-(1-phenylmethylpyrazol-5-yl) anthranilic acid, m.p. 190° C.

Workup

  1. temperatureis refluxed for about 2 days
  2. filtrationthe solid which forms is collected by filtration
  3. washwashed with water
  4. dry with materialether and then is dried

Sources & evidence

ORD record
ord-e47546492d09462da4b23d0390dc2316
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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