Sodium Chloride → 5-[4-(6-Fluoro-2-quinolyloxy)phenoxy]2,4-hexanedione

HRID 1248083

Reaction equation

HRID 1248083 reaction equation
[C:1]([CH:4]([C:9](=[O:31])[CH:10]([O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[C:25]([F:30])[CH:26]=3)[N:21]=2)=[CH:15][CH:14]=1)[CH3:11])C(OC)=O)(=[O:3])[CH3:2].[H][H].FC1C=C2C(=CC=1)N=C(OC1C=CC(OC(C)C(Cl)=O)=CC=1)C=C2.[Na].COC(=O)CC(C)=O.C([O-])(=O)CCCC.[Cl-].[Na+]>CS(C)=O>[F:30][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[N:21]=[C:20]([O:19][C:16]1[CH:15]=[CH:14][C:13]([O:12][CH:10]([CH3:11])[C:9](=[O:31])[CH2:4][C:1](=[O:3])[CH3:2])=[CH:18][CH:17]=1)[CH:29]=[CH:28]2

Participants

9

Reactant 7

HCID 5234Sodium ChlorideHCID 7757Methyl acetoacetateHCID 114781ValerateHCID 5360545SodiumHCID 150701622-(4-((6-Fluoro-2-quinolinyl)oxy)phenoxy)propionyl chlorideHCID 20278379Methyl 2-acetyl-4-[4-(6-fluoro-2-quinolyloxy)phenoxy]-3-oxopentanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 202783925-[4-(6-Fluoro-2-quinolyloxy)phenoxy]2,4-hexanedione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In the same manner, methyl 2-acetyl-4-[4-(6-fluoro-2-quinolyloxy)phenoxy]-3-oxopentanoate (XII; X' is fluoro and X" is hydrogen) is prepared from 2-[4-(6-fluoro-2-quinolyloxy)phenoxy]propionic acid chloride and the sodium salt of methylacetoacetate. This pentanoate is then heated with sodium chloride and DMSO to give 5-[4-(6-fluoro-2-quinolyloxy)phenoxy]2,4-hexanedione (XIII; X' is fluoro and X" is hydrogen).

Sources & evidence

ORD record
ord-5dd37180b95f49ccae12bf69a9dafdee
Source dataset
uspto-grants-1985_06
Patent number
US04522647

Linked notes

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