Hexane → HCID 178477332, compound

HRID 1949166Notes

Reaction equation

HRID 1949166 reaction equation
C[Al](C)C.[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9][NH2:10].C([O:16][C:17]([C:19]1[C:20]([S:34][CH2:35][CH3:36])=[N:21][C:22]2[C:27]([C:28]=1[OH:29])=[CH:26][CH:25]=[C:24]([C:30]([F:33])([F:32])[F:31])[CH:23]=2)=O)C.CCCCCC>C1(C)C=CC=CC=1.O>[CH2:35]([S:34][C:20]1[C:19]([C:17]([NH:10][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[C:6]([F:5])[CH:7]=2)=[O:16])=[C:28]([OH:29])[C:27]2[C:22](=[CH:23][C:24]([C:30]([F:33])([F:31])[F:32])=[CH:25][CH:26]=2)[N:21]=1)[CH3:36]

Participants

7

Reactant 4

HCID 8058HexaneHCID 668533-FluorobenzylamineHCID 16682925TrimethylaluminumHCID 178470103HCID 178470103, compound

Product 1

HCID 178477332HCID 178477332, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

5.8 ml (11.6 mmol, 2M in toluene)trimethyl aluminium and 1.5 g (11.6 mmol) 3-fluorobenzylamine were added in succession to a solution of 1.0 g (2.9 mmol) 2-(ethylthio)-4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester in toluene (18 ml) and the mixture was then heated for 2 h at 80° C. Then it was diluted with water and extracted with EE. The organic phase was washed with 1M hydrochloric acid, water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 17:3) of the residue yielded 0.9 g (2.1 mmol, 73%) 2-(ethylthio)-N-(3-fluorobenzyl)-4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxamide.

Workup

  1. extractionextracted with EE
  2. washThe organic phase was washed with 1M hydrochloric acid, water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-12e48b8c9de04d9f8f2d972ad435c016
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

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