Triethylamine → HCID 178515070, compound

HRID 1600046Notes

Reaction equation

HRID 1600046 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.[Br: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>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[C:3](=[O:4])[C:5]3[NH:6][C:7]4[CH:8]=[C:9]([Cl:20])[CH:10]=[CH:11][C:12]=4[C:13](=[O:19])[C:14]=3[C:15]([OH:17])=[N:30]2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 121574-Bromophenylhydrazine hydrochlorideHCID 178418477HCID 178418477, compound

Product 1

HCID 178515070HCID 178515070, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of dimethyl7-chloro-4-hydroxyquinoiine-2,3-dicarboxylate (1.90 g, 6.40 mM) and 4-bromophenyi hydrazine hydrochloride (10.0 g, 44.7 mM) in ethanol (35mL) was added triethylamine (7.1 mL, 51.1 mM). The resulting brown solutionwas refluxed for 22 hours during which time a tan precipitate formed. This mixture was cooled to room temperature and filtered to give the 4-bromophenyl hydrazine salt of the title compound as a white powder (1.69g). This material was refluxed in glacial acetic acid (20 mL) for 3 hours and cooled to room temperature. The resulting tan suspension was filtered and the solids washed with glacial acetic acid and then ether to give the title compound (1.15 g, 43%) as a tan powder, mp 393°-394° C.; MS(CI): 420 (M+H).

Workup

  1. temperatureThe resulting brown solutionwas refluxed for 22 hours during which time a tan precipitate
  2. customformed
  3. filtrationfiltered

Sources & evidence

ORD record
ord-ab10d50bb36542b8955b34ae3ee0f200
Source dataset
uspto-grants-1998_04
Patent number
US05744471

Reaction notes

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