3-Fluorobenzylamine → HCID 86645341, compound

HRID 1949158Notes

Reaction equation

HRID 1949158 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].[Cl:10][C:11]1[C:20]([C:21](Cl)=[O:22])=[C:19]([CH3:24])[C:18]2[C:13](=[CH:14][C:15]([C:25]([F:28])([F:27])[F:26])=[CH:16][CH:17]=2)[N:12]=1>O1CCOCC1>[Cl:10][C:11]1[C:20]([C:21]([NH:6][CH2:5][C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=2)=[O:22])=[C:19]([CH3:24])[C:18]2[C:13](=[CH:14][C:15]([C:25]([F:26])([F:28])[F:27])=[CH:16][CH:17]=2)[N:12]=1

Participants

4

Reactant 2

HCID 668533-FluorobenzylamineHCID 86645342HCID 86645342, compound

Product 1

HCID 86645341HCID 86645341, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2.9 g (23.4 mmol) 3-fluorobenzylamine was added dropwise at RT to a solution of 6.0 g (19.5 mmol) 2-chloro-4-methyl-7-(trifluoromethyl)quinoline-3-carbonyl chloride in dioxane (35 ml). The mixture was then stirred for 60 min at RT and then quenched with water. The reaction solution was extracted with EE and the organic phase was washed with a 1M aqueous NH4Cl solution and brine, dried over MgSO4, filtered and concentrated to small volume under vacuum. Crystallisation of the residue (EE) yielded 6.4 g (16.1 mmol, 83%) 2-chloro-N-[(3-fluorophenyl)-methyl]-4-methyl-7-(trifluoromethyl)-quinoline-3-carboxamide.

Workup

  1. customquenched with water
  2. extractionThe reaction solution was extracted with EE
  3. washthe organic phase was washed with a 1M aqueous NH4Cl solution and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to small volume under vacuum
  7. customCrystallisation of the residue (EE)

Sources & evidence

ORD record
ord-da3350f63a4d4c50a970728c79372f0b
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

Loading…