Dimethylformamide → HCID 19592214, compound

HRID 1458741Notes

Reaction equation

HRID 1458741 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH3:8])[N:5]=[C:4]([CH3:9])[CH:3]=1.I[C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C>[CH2:7]([N:6]1[C:2]([NH:1][C:11]2[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:13]([OH:15])=[O:14])=[CH:3][C:4]([CH3:9])=[N:5]1)[CH3:8]

Participants

6

Reactant 4

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

Product 1

HCID 19592214HCID 19592214, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5-amino-1-ethyl-3-methylpyrazole (7.5 g, 0.06 mol), 2-iodobenzoic acid (14.88 g, 0.06 mol), DMF (50 ml) Cu(OAc)2.H2O (0.5 g) and K2CO3 (8.3 g, 0.06 mol) is refluxed under a nitrogen atmosphere for 20 hours. The reaction mixture is cooled to room temperature and then is poured into ice water. The mixture is neutralized with acetic acid, and the resulting solid is collected by filtration, washed with water and dried to afford 7.1 g (48%) of N-(1-ethyl-3-methylpyrazol-5-yl)anthranilic acid.

Workup

  1. temperatureis refluxed under a nitrogen atmosphere for 20 hours
  2. filtrationthe resulting solid is collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-fe0e1cbafa33441e9e626e81d7ec1d4b
Source dataset
uspto-grants-1998_12
Patent number
US05852035

Reaction notes

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