Piperidine → HCID 45089600, compound

HRID 1993099Notes

Reaction equation

HRID 1993099 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11]([O:16][CH3:17])(=[O:15])[C:12]([CH3:14])=O.N1CCCCC1>CO>[CH3:17][O:16][C:11]([C:12]1[CH:14]=[CH:4][C:3]2[C:2](=[CH:9][C:8]([NH2:10])=[CH:7][CH:6]=2)[N:1]=1)=[O:15]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11748Methyl pyruvateHCID 111477482,4-Diaminobenzaldehyde

Product 1

HCID 45089600HCID 45089600, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

For example, 2,4-diaminobenzaldehyde 53.7 (Apin Chemicals) is reacted with one molar equivalent of methyl pyruvate 53.2 in methanol, in the presence if a base such as piperidine, to afford methyl-7-aminoquinoline-2-carboxylate 53.8. Basic hydrolysis of the product, employing one molar equivalent of lithium hydroxide in aqueous methanol, then yields the carboxylic acid 53.9. The amino-substituted carboxylic acid is then converted into the diazonium tetrafluoborate 53.10 by reaction with sodium nitrite and tetrafluoboric acid. The diazonium salt is heated in aqueous solution to afford the 7-hydroxyquinoline-2-carboxylic acid, 53.11, Z=OH. Alternatively, the diazonium tetrafluoborate is heated in aqueous organic solution with one molar equivalent of cuprous bromide and lithium bromide, to afford 7-bromoquinoline-2-carboxylic acid 53.11, X═Br. Alternatively, the diazonium tetrafluoborate 53.10 is reacted in acetonitrile solution with the sulfhydryl form of an ion exchange resin, as described in Sulfur Lett., 2000, 24, 123, to prepare 7-mercaptoquinoline-2-carboxylic acid 53.11, Z=SH.

Sources & evidence

ORD record
ord-a87e5c8c16e84277aebb27e30d620f96
Source dataset
uspto-grants-2010_01
Patent number
US07649015B2

Reaction notes

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