2-Iodobenzoic acid → HCID 19592225, compound

HRID 1458733Notes

Reaction equation

HRID 1458733 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]([CH:23]([CH3:25])[CH3:24])[N:21]=[CH:20][CH:19]=1>CN(C=O)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH: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)([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 69412-Iodobenzoic acidHCID 11430Potassium CarbonateHCID 10903411-(propan-2-yl)-1H-pyrazol-5-amine

Product 1

HCID 19592225HCID 19592225, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 6228DimethylformamideSolvent

Procedure

To 2-iodobenzoic acid (54 g, 0.218 mol) in DMF (570 ml) is added K2CO3 (33.4 g, 0.242 mol), then 5-amino-1-isopropylpyrazole (27.3 g, 0.218 mol) and finally copper (II) acetate monohydrate (0.9 g, 4.5 mmol). The reaction mixture is refluxed overnight and then the DMF is evaporated. The residue is poured into ice/water and then the mixture is acidified with acetic acid and concentrated HCl to a pH of about 4. A precipitate forms which is collected by filtration, washed with water and dried in a vacuum oven at 40° C. to afford 52 g (97.2%) of N-(1-isopropylpyrazol-5-yl)anthranilic acid.

Workup

  1. temperatureThe reaction mixture is refluxed overnight
  2. customthe DMF is evaporated
  3. additionThe residue is poured into ice/water
  4. filtrationA precipitate forms which is collected by filtration
  5. washwashed with water
  6. customdried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-6e5981c6ce6d42c487d91edeb0229335
Source dataset
uspto-grants-1998_12
Patent number
US05852035

Reaction notes

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