Pyridine → 6-Hydroxy-2-oxo-1,2-dihydroquinoline-5-carbaldehyde

HRID 579469

Reaction equation

HRID 579469 reaction equation
BrC1C(=O)[O:4][C:5]2[C:10](C=1C)=[CH:9]C=[C:7]([OH:13])[CH:6]=2.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[O:21](C(C(F)(F)F)=O)C(C(F)(F)F)=O>C(Cl)Cl>[OH:4][C:5]1[CH:10]=[CH:9][C:20]2[NH:15][C:16](=[O:21])[CH:17]=[CH:18][C:19]=2[C:6]=1[CH:7]=[O:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 53375453-Bromo-7-hydroxy-4-methylchromen-2-one

Product 1

HCID 866834296-Hydroxy-2-oxo-1,2-dihydroquinoline-5-carbaldehydeYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Compound 1 (38 g, 249.6 mmol) and pyridine (21.7 g, 275.0 mmol) were dissolved in DCM (750 mL). (CF3CO)2O (57.7 g, 275.0 mmol) was added dropwise at 0° C. After that the reaction mixture was stirred at RT for 16 h. The reaction mixture was diluted with DCM (500 mL), washed with 1N HCl, concentrated. The residue was purified by silica gel column (PE:EA=10:1), afforded compound 2 (45 g, 72%) as white solid.

Workup

  1. washwashed with 1N HCl
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column (PE:EA=10:1)

Sources & evidence

ORD record
ord-e66b7c0178974a83b40a588fcf4809cb
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Linked notes

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