Triethylamine → HCID 178515078, compound

HRID 323616

Reaction equation

HRID 323616 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.Cl.[CH2:23]([NH:30][NH2:31])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C>C(O)C>[CH2:23]([N:30]1[C:15](=[O:17])[C:14]2[C:13](=[O:19])[C:12]3[CH:11]=[CH:10][C:9]([Cl:20])=[CH:8][C:7]=3[NH:6][C:5]=2[C:3]([OH:4])=[N:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 146540Benzylhydrazine dihydrochlorideHCID 178418477HCID 178418477, compound

Product 1

HCID 178515078HCID 178515078, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of dimethyl-7-chloro-4-hydroxyquinoline-2,3-dicarboxylate (5.00 g, 16.90 mM) and benzylhydrazine dihydrochloride (46.15 g, 236.50 mM) in ethanol (100 mL) was added triethylamine (75.8 mL, 541.0 mM). The mixture was heated to give a brown solution which was refluxed for 40 hours during which time a precipitate formed. The suspension was cooled to room temperature and filtered to give the benzylhydrazine salt of the title compound as an impure yellow solid. Multiple crystallizations from ethanolic hydrogen chloride and methanol gave the title compound (0.370 g, 6%) as a white powder, mp 347-350° C.; MS(CI): 354 (M+H).

Workup

  1. temperatureThe mixture was heated
  2. customto give a brown solution which
  3. temperaturewas refluxed for 40 hours during which time a precipitate
  4. customformed
  5. filtrationfiltered

Sources & evidence

ORD record
ord-f8c16bbecf424a2f81a68afe47b94588
Source dataset
uspto-grants-2001_04
Patent number
US06214826B1

Linked notes

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