Hydrochloric Acid → 2-((1-Ethyl-1H-pyrazol-5-yl)amino)benzoic acid

HRID 1586128Notes

Reaction equation

HRID 1586128 reaction equation
I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[NH2:17][C:18]1[N:22]([CH2:23][CH3:24])[N:21]=[CH:20][CH:19]=1.Cl>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Cu+2].O.C(O)(=O)C>[CH2:23]([N:22]1[C:18]([NH:17][C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:19][CH:20]=[N:21]1)[CH3:24]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 69412-Iodobenzoic acidHCID 11430Potassium CarbonateHCID 3373101-Ethyl-1H-pyrazol-5-amine

Product 1

HCID 154274682-((1-Ethyl-1H-pyrazol-5-yl)amino)benzoic acidYield 42.4%

Reagents, catalysts & solvents 3

HCID 165397Cupric acetate monohydrateCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-iodobenzoic acid (54 g, 0.218 mol) in DMF (570 ml) is added potassium carbonate (33.4 g, 0.242 mol), followed by 5-amino-1-ethylpyrazole (24.2 g, 0.218 mol) and finally Cu(OAc)2.H2O (0.9 g, 0.0045 mol). The reaction mixture is refluxed overnight, cooled and then poured into ice water. Acetic acid and HCl are added until a pH of about 4 is obtained. A precipitate forms which is collected by filtration, washed with water and dried to afford 21.4 g of N-(1-ethylpyrazol-5-yl) anthranilic acid.

Workup

  1. temperatureThe reaction mixture is refluxed overnight
  2. temperaturecooled
  3. customis obtained
  4. filtrationA precipitate forms which is collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-22aac3f4894442f5ba4a2651c4f6fb45
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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