2-Iodobenzoic acid → HCID 19592225, compound

HRID 977125Notes

Reaction equation

HRID 977125 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) was 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 was refluxed overnight and then the DMF was evaporated. The residue was poured into ice/water and then the mixture was acidified with acetic acid and concentrated HCl to a pH of about 4. A precipitate formed which was 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 was refluxed overnight
  2. customthe DMF was evaporated
  3. additionThe residue was poured into ice/water
  4. customA precipitate formed which
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-ff6193744e8d482e82dea09297d17b73
Source dataset
uspto-grants-1997_03
Patent number
US05614530

Reaction notes

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