Triethylamine → HCID 178515070, compound

HRID 323632Notes

Reaction equation

HRID 323632 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 dimethyl-7-chloro-4-hydroxyquinoline-2,3-dicarboxylate (1.90 g, 6.40 mM) and 4-bromophenylhydrazine hydrochloride (10.0 g, 44.7 mM) in ethanol (35 mL) was added triethylamine (7.1 mL, 51.1 mM). The resulting brown solution was refluxed for 22 hours during which time a tan precipitate formed. This mixture was cooled to room temperature and filtered to give the 4-bromophenylhydrazine salt of the title compound as a white powder (1.69 g). 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 solution was refluxed for 22 hours during which time a tan precipitate
  2. customformed
  3. filtrationfiltered

Sources & evidence

ORD record
ord-c627624004954f88939d04c208eaa6a9
Source dataset
uspto-grants-2001_04
Patent number
US06214826B1

Reaction notes

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