Dimethylformamide → N-(1-cyclopentylpyrazol-5-yl) anthranilic acid

HRID 375860

Reaction equation

HRID 375860 reaction equation
I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:11][C:12]1[N:16]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:15]=[CH:14][CH:13]=1.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[CH:17]1([N:16]2[C:12]([NH:11][C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]([OH:6])=[O:5])=[CH:13][CH:14]=[N:15]2)[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 69412-Iodobenzoic acidHCID 11430Potassium CarbonateHCID 10797921-cyclopentyl-1H-pyrazol-5-amine

Product 1

HCID 54038843N-(1-cyclopentylpyrazol-5-yl) anthranilic acidYield 68.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-iodobenzoic acid (28 g, 0.113 mol), 5-amino-1-cyclopentylpyrazole (17 g, 0.113 mol), DMF (100 ml), potassium carbonate (16 g, 0.113 mol) and Cu(OAc) 2 (0.5 g) was refluxed overnight. The reaction mixture was poured into ice-water, and acidified with acetic acid to a pH of 5. The gum which formed was extracted with CH2Cl2 and the CH2Cl2 layer was washed with water, dried over MgSO4, and evaporated to afford 21 g of N-(1-cyclopentyl pyrazol-5-yl) anthranilic acid.

Workup

  1. temperaturewas refluxed overnight
  2. customThe gum which formed
  3. extractionwas extracted with CH2Cl2
  4. washthe CH2Cl2 layer was washed with water
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-24c745ae42994c5db88ebabca4b6f325
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Linked notes

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