Triethylamine → HCID 178492080, compound

HRID 323611Notes

Reaction equation

HRID 323611 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.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][NH2:31])=[CH:26][CH:25]=1.C(N(CC)CC)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:31][N:30]([C:27]4[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=4)[C:3](=[O:4])[C:5]=3[NH:6][C:7]=2[CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 178418477HCID 178418477, compound

Product 1

HCID 178492080HCID 178492080, compoundYield 112%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of dimethyl-7-chloro-4-hydroxyquinoline-2,3-dicarboxylate (0.500 g, 1.69 mM) in ethanol (17 mL) was added 4-methoxyphenylhydrazine hydrochloride (2.07 g, 11.83 mM). Triethylamine (1.88 mL, 13.52 mM) was added, and the mixture was heated to reflux for 40 hours. The resulting suspension was filtered hot, and the collected solids were washed with ethanol to give the 4-methoxyphenylhydrazine salt of the title compound (0.700 g) as a light tan solid. This material was heated to reflux in glacial acetic acid (20 mL) for 2 hours to give a brown suspension. The suspension was cooled to room temperature. The solids were collected and washed with glacial acetic acid, methanol and ether to give the title compound (0.331 g, 53%) as a tan powder, mp 365° C. (decomp.); MS(CI): 370 (M+H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 40 hours
  3. filtrationThe resulting suspension was filtered hot
  4. washthe collected solids were washed with ethanol

Sources & evidence

ORD record
ord-d8c71fcde16d4413a74a78d84c266803
Source dataset
uspto-grants-2001_04
Patent number
US06214826B1

Reaction notes

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