Heptane → HCID 178524447, compound

HRID 478653

Reaction equation

HRID 478653 reaction equation
C(O[C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])C.[NH:17]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)[NH2:18].CCCCCCC>C(O)CCC>[O:5]=[C:4]1[C:6]2=[CH:7][NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:15]2=[N:18][N:17]1[C:19]1[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8900HeptaneHCID 120894-Hydrazinobenzoic acidHCID 268963Ethyl 4-Chloroquinoline-3-carboxylate

Product 1

HCID 178524447HCID 178524447, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 4-chloro-quinoline-3-carboxylic acid ethyl ester (11.8 mg, 0.5 mmol) and 4-hydrazino-benzoic acid (7.6 mg, 0.5 mmol) in n-butanol (0.5 mL) was stirred at 115° C. over night in a sealed tube. After cooling to 50-70° C., heptane (1.0 mL) was added and the product was allowed to crystallize upon further cooling to room temperature. The solvent was removed and the product was washed with heptane and dried under vacuum to yield 4-(3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl)-benzoic acid (13 mg). 1H NMR (400 MHz, DMSO-d6) δ 12.9 (1H, s), 8.77 (1H, d), 8.38 (2H, d), 8.25 (1H, d), 8.03 (2H, d), 7.65-7.77 (2H, m), 7.58 (1H, t).

Workup

  1. customto crystallize
  2. temperatureupon further cooling to room temperature
  3. customThe solvent was removed
  4. washthe product was washed with heptane
  5. customdried under vacuum

Sources & evidence

ORD record
ord-69af56a780f04c518b22da7aedf8bfda
Source dataset
uspto-grants-2003_11
Patent number
US06642249B2

Linked notes

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