2-Hydroxyquinoline → HCID 19918917, compound

HRID 1648203Notes

Reaction equation

HRID 1648203 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:15]=[C:16]1O[C:18](=[O:19])[CH2:17]1.N1C2C(=CC=CC=2)C=CC1=O>C(O)(=O)C.S(=O)(=O)(O)O>[CH3:1][N:2]1[C:3]2[C:8](=[CH:7][CH:6]=[CH:5][C:4]=2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:16]([CH3:15])=[CH:17][C:18]1=[O:19]

Participants

5

Reactant 3

HCID 60382-HydroxyquinolineHCID 12661DiketeneHCID 12246986N-Methylbiphenyl-2-amine

Product 1

HCID 19918917HCID 19918917, compound

Reagents, catalysts & solvents 1

HCID 23350293Acetic acid sulfuric acidSolvent

Procedure

The starting material is 2-phcnylaniline, which is methylated with potassium carbonate and methyl iodide to obtain N-methyl-2-phenylaniline. The N-methyl-2-phenylaniline is treated with diketene and acid and is cyclized in acetic acid/sulfuric acid as in Example 3 to generate the desired quinolone.

Sources & evidence

ORD record
ord-828071d3eb02426783cb8203d20b079c
Source dataset
uspto-grants-1995_07
Patent number
US05436134

Reaction notes

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