Dimethylformamide → HCID 19592214, compound

HRID 1586131Notes

Reaction equation

HRID 1586131 reaction equation
I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:11]([N:13]1[C:17]([NH2:18])=[CH:16][C:15]([CH3:19])=[N:14]1)[CH3:12].CN(C=O)C.C(=O)([O-])[O-].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C.O>[CH2:11]([N:13]1[C:17]([NH:18][C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:16][C:15]([CH3:19])=[N:14]1)[CH3:12]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 69412-Iodobenzoic acidHCID 11430Potassium CarbonateHCID 27683831-Ethyl-3-methyl-1H-pyrazol-5-amine

Product 1

HCID 19592214HCID 19592214, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 2-iodobenzoic acid (14.88 g, 0.06 mol), 1-ethyl-3-methyl-5-aminopyrazole (7.5 g, 0.06 mol), DMF (50 ml), Cu(OAc)2. H2O (0.5 g) and potassium carbonate (8.3 g, 0.06 mol) is refluxed for 20 hours. The reaction mixture is cooled to room temperature, poured into ice waterl and neutralized with acetic acid. A solid forms which is collected by filtration, washed with water and dried to give 7.1 g (98%) of N-(1-ethyl-3-methylpyrazol-5-yl) anthranilic acid.

Workup

  1. additionpoured into ice waterl
  2. filtrationA solid forms which is collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-0bd142b2bed14181b0867b7f332a69c1
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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