3-chloro-5-(trifluoromethyl)benzoic Acid → HCID 70663316, compound

HRID 878104Notes

Reaction equation

HRID 878104 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15].[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[C:20]([OH:22])=O>>[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[C:20]([N:2]([CH3:1])[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])=[O:22]

Participants

3

Reactant 2

HCID 38023623-chloro-5-(trifluoromethyl)benzoic AcidHCID 18403336N-methyl-4-o-tolylpyridin-3-amine

Product 1

HCID 70663316HCID 70663316, compound

Procedure

The title compound was prepared in analogy to example 90, from N-methyl-4-o-tolylpyridin-3-amine (example 1, intermediate a) and 3-chloro-5-(trifluoromethyl)benzoic acid (CAS RN 39226-97-6) after a reaction time of 68 hours. The compound was purified by silica gel chromatography on a 10 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 30:70). The product-containing fractions were pooled and evaporated. The product was dissolved in EtOAc and extracted three time with 1M aqueous HCl. The organic layers were washed with brine, dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified a second time by silica gel chromatography on a 10 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 30:70). Light brown solid (47%). MS (ESI): m/z=405.10 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 10 g column
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 30:70)
  3. customevaporated
  4. dissolutionThe product was dissolved in EtOAc
  5. extractionextracted three time with 1M aqueous HCl
  6. washThe organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. additiontreated with silica gel
  10. customevaporated
  11. customThe compound was purified a second time by silica gel chromatography on a 10 g column
  12. washeluting with a gradient of n-heptane:EtOAc (100:0 to 30:70)

Sources & evidence

ORD record
ord-1db7b41fb3294a84b82d5fca6f7e8fdd
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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