3-Nitro-5-(trifluoromethyl)benzoic acid → HCID 70663518, compound

HRID 878206Notes

Reaction equation

HRID 878206 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].[N+:16]([C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[C:22](O)=[O:23])([O-:18])=[O:17]>>[CH3:1][N: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])[C:22](=[O:23])[C:21]1[CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=[C:19]([N+:16]([O-:18])=[O:17])[CH:20]=1

Participants

3

Reactant 2

HCID 6166023-Nitro-5-(trifluoromethyl)benzoic acidHCID 18403336N-methyl-4-o-tolylpyridin-3-amine

Product 1

HCID 70663518HCID 70663518, 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-nitro-5-trifluoromethyl-benzoic acid (CAS RN 328-80-3) after a reaction time of 48 hours. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:80). The product-containing fractions were pooled and concentrated under vacuum. The residue was dissolved in 30 mL 1M aqueous HCl and 30 mL EtOAc and the layers were separated. The aqueous layer was extracted a second time with 30 mL EtOAc. The organic layers were washed twice with 30 mL 1M aqueous HCl and with 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. Light yellow solid (66%). MS (ESI): m/z=416.121 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:80)
  3. concentrationconcentrated under vacuum
  4. dissolutionThe residue was dissolved in 30 mL 1M aqueous HCl
  5. custom30 mL EtOAc and the layers were separated
  6. extractionThe aqueous layer was extracted a second time with 30 mL EtOAc
  7. washThe organic layers were washed twice with 30 mL 1M aqueous HCl and with 30 mL brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ab0970d9c91041b3a52eb1a4c2ceca88
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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