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

HRID 375844Notes

Reaction equation

HRID 375844 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) was 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 was refluxed overnight, cooled and then poured into ice-water. Acetic acid and HCl were added until a pH of about 4 was obtained. A precipitate formed which was 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 was refluxed overnight
  2. temperaturecooled
  3. customwas obtained
  4. customA precipitate formed which
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-13a1490ccfee48f5a6f304116bcedf54
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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