3-Fluorobenzylamine → HCID 178467384, compound

HRID 242123Notes

Reaction equation

HRID 242123 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]([O: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.CCOC(C)=O.CCCCCC>C1(C)C=CC=CC=1.O>[CH2:35]([O: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 668533-FluorobenzylamineHCID 16682925TrimethylaluminumHCID 21226206Ethyl acetate hexaneHCID 178470038HCID 178470038, compound

Product 1

HCID 178467384HCID 178467384, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

1.5 ml (3.0 mmol, 2M in toluene)trimethylaluminium and 350 μl (3.0 mmol) 3-fluorobenzylamine were added consecutively at RT to a solution of 500 mg (1.5 mmol) 2-ethoxy-4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester in toluene (10 ml). The RS was subsequently heated to 80° C. for 4 h. The mixture was subsequently diluted with water and extracted with EtOAc. The organic phase was washed with water and brine, dried over Na2SO4 and concentrated in a vacuum. After CC (EtOAc/hexane 1:9) of the residue, 250 mg (0.6 mmol, 41%) 2-ethoxy-N-(3-fluorobenzyl)-4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxylic acid amide was obtained.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-f3609a0d1bfb40db82cbbd054a5c890c
Source dataset
uspto-grants-2014_02
Patent number
US08653101B2

Reaction notes

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