Triethylamine → HCID 178515073, compound

HRID 323630Notes

Reaction equation

HRID 323630 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(O)C.C(OCC)(=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 3

HCID 8471TriethylamineHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 178418477HCID 178418477, compound

Product 1

HCID 178515073HCID 178515073, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of dimethyl-7-chloro-4-hydroxyquinoline-2,3-dicarboxylate (2.59 g, 8.79 mM) and 4-fluorophenylhydrazine 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 diluted with 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 successively with ethyl acetate/ether and ether to give the 4-fluorophenylhydrazine salt of the title compound (2.14 g). This material was refluxed in glacial acetic 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. customto give a white crystalline precipitate which
  3. customwas removed by filtration
  4. washThe filtrate was washed with hydrochloric acid (3×500 mL, 1N) which
  5. customprecipitation in the ethyl acetate layer
  6. customThe precipitate was collected
  7. washwashed successively with ethyl acetate/ether and ether

Sources & evidence

ORD record
ord-dfaa170228c94ec19c8fde76256d6ca0
Source dataset
uspto-grants-2001_04
Patent number
US06214826B1

Reaction notes

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