Triethylamine → HCID 178426277, compound

HRID 1600039Notes

Reaction equation

HRID 1600039 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). Analysis for C18 H12ClN3O3 ·0.2H2O: Calculated: C, 60.49; H, 3.50; N, 11.76; Found: C, 60.66; H, 3.26; N, 11.76; NMR: 13.81 (v br s,1H exchangeable), 8.39 (s, 1H exchangeable), 8.22 (d, J=8.58 Hz, 1H), 7.89 (d, J=1.97 Hz, 1H), 7.58 (dd, J=1.97, 8.58 Hz, 1H), 6.98 (d, J=8.28 Hz, 2H), 6.73 (d, J=8.28 Hz, 2H), 2.19 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-05ce601d10e44a82862866816df6f08e
Source dataset
uspto-grants-1998_04
Patent number
US05744471

Reaction notes

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