Triethylamine → HCID 178426277, compound

HRID 1977210Notes

Reaction equation

HRID 1977210 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:20])=[C:7]([C:16]([O:18]C)=O)[C:8]([C:12]([O:14]C)=O)=[N:9]2)=[CH:4][CH:3]=1.Cl.[CH3:22][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>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:20])[C:7]3[C:16]([OH:18])=[N:30][N:29]([C:26]4[CH:27]=[CH:28][C:23]([CH3:22])=[CH:24][CH:25]=4)[C:12](=[O:14])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 178418477HCID 178418477, compound

Product 1

HCID 178426277HCID 178426277, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of dimethyl 7-chloro-4-hydroxyquinoline-2,3-dicarboxylate (3.90 g, 13.3 mM) and 4-methylphenyl hydrazine hydrochloride (14.8 g, 93.2 mM) in ethanol (140 mL) was added triethylamine (14.8 mL, 106.4 mM). The resulting brown solution was refluxed for 16 hours during which time a precipitate formed. The resulting suspension was cooled to room temperature and filtered to give the 4-methylphenyl hydrazine salt of the title compound as a grey powder (2.30 g). This material was refluxed in glacial acetic acid (45 mL) for 2 hours and cooled to room temperature. The resulting brown suspension was filtered to give the title compound (1.60 g, 34%) as a tan powder, mp 380-382° C.; MS(CI): 354 (M+H).

Workup

  1. temperatureThe resulting brown solution was refluxed for 16 hours during which time a precipitate
  2. customformed
  3. filtrationfiltered

Sources & evidence

ORD record
ord-4c42a8d9ad6142a6841248be5d7a7c30
Source dataset
uspto-grants-2001_05
Patent number
US06232313B1

Reaction notes

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