Triethylamine → HCID 178515073, compound

HRID 1600044Notes

Reaction equation

HRID 1600044 reaction equation
CO[C:3]([C:5]1[C:14]([C:15]([O:17]C)=O)=[C:13]([OH:19])[C:12]2[C:7](=[CH:8][C:9]([Cl:20])=[CH:10][CH:11]=2)[N:6]=1)=[O:4].Cl.[F:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][NH2:30])=[CH:25][CH:24]=1.C(N(CC)CC)C.C(OCC)(=O)C>C(O)C>[Cl:20][C:9]1[CH:10]=[CH:11][C:12]2[C:13](=[O:19])[C:14]3[C:15]([OH:17])=[N:30][N:29]([C:26]4[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=4)[C:3](=[O:4])[C:5]=3[NH:6][C:7]=2[CH:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 178418477HCID 178418477, compound

Product 1

HCID 178515073HCID 178515073, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of dimethyl7-chloro-4-hydroxyquinoline-2,3-dicarboxylate (2.59 g, 8.79 mM) and 4-fluorophenyl hydrazine hydrochloride (10.0 g, 61.5 mM) in ethanol (48 mL) was added triethylamine (9.8 mL, 70.3 mM). The resulting brown solution was refluxed for 48 hours, cooled to room temperature and dilutedwith ethyl acetate (150 mL) to give a white crystalline precipitate which was removed by filtration and discarded. The filtrate was washed with hydrochloric acid (3×500 mL, 1N) which caused precipitation in the ethyl acetate layer. The precipitate was collected and washed successivelywith ethyl acetate/ether and ether to give the 4-fluorophenyl hydrazine salt of the title compound (2.14 g). This material was refluxed in glacialacetic acid (20 mL) for 2 hours. After cooling the acetic acid solution to room temperature, a precipitate formed and the solids were collected to give the title compound (1.48 g, 47%) as a yellow powder, mp 390°-392° C.; MS(CI): 358 (M+H).

Workup

  1. temperatureThe resulting brown solution was refluxed for 48 hours
  2. customwas removed by filtration
  3. washThe filtrate was washed with hydrochloric acid (3×500 mL, 1N) which
  4. customprecipitation in the ethyl acetate layer
  5. customThe precipitate was collected
  6. washwashed successivelywith ethyl acetate/ether and ether

Sources & evidence

ORD record
ord-8f42553f1b904fd5a36cefa78517b092
Source dataset
uspto-grants-1998_04
Patent number
US05744471

Reaction notes

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