Methyl iodide → HCID 15075811, compound

HRID 2073822Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]1[O:11][CH2:12][C:13]([CH3:16])([CH3:15])[N:14]=1.[CH:17]([N-]C(C)C)(C)C.[Li+].CI>>[F:1][C:2]1[C:7]([CH3:17])=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]1[O:11][CH2:12][C:13]([CH3:16])([CH3:15])[N:14]=1

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 2724682Lithium diisopropylamide

HCID 110097344,4-Dimethyl-2-(2,4,5-trifluorophenyl)-4,5-dihydro-1,3-oxazole

Product 1

HCID 15075811HCID 15075811, compound

Procedure

The 2-(2,4,5-trifluorophenyl)-4,4-dimethyl-2-oxazoline was also treated with lithium diisopropylamide followed by methyl iodide to give 2-(2,4,5-trifluoro-3-methylphenyl)-4,4-dimethyl-2-oxazoline. This intermediate was, in turn, treated with lithium diisopropylamide, then with methyl iodide, to give 2-(2,4,5-trifluoro-3,6-dimethylphenyl)-4,4-dimethyl-2-oxazoline. Hydrolysis of the oxazoline gave 2,4,5-trifluoro-3,6-dimethylbenzoic acid, which was elaborated into 1-cyclopropyl-6,7-difluoro-1,4-dihydro-5,8-dimethyl-4-oxo-3-quinolinecarboxylic acid in the usual manner.

Sources & evidence

ORD record: ord-9ee9189ccc7148b9a8572aa4d4944e50
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04920120

Reaction notes

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