Dimethylformamide → HCID 19592214, compound

HRID 375847Notes

Reaction equation

HRID 375847 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].O.C(O)(=O)C>[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

7

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 2

HCID 165397Cupric acetate monohydrateCatalystHCID 176Acetic AcidSolvent

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) was refluxed for 20 hours. The reaction mixture was cooled to room temperature, poured into ice-water and neutralized with acetic acid. A solid formed which was 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. temperaturewas refluxed for 20 hours
  2. customA solid formed which
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-7454704f60244e45a52b96b61b3a2ef0
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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