Hydrochloric Acid → 2-Methyl-3-nitro-5-(trifluoromethyl)pyridine

HRID 1098596Notes

Reaction equation

HRID 1098596 reaction equation
[N+:1]([C:4]1[C:5]([CH:14](C(OC)=O)C(OC)=O)=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].Cl.[OH-].[Na+]>CCOC(C)=O>[CH3:14][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][C:8]([C:10]([F:12])([F:11])[F:13])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66729193HCID 66729193, compound

Product 1

HCID 233805732-Methyl-3-nitro-5-(trifluoromethyl)pyridineYield 25.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dimethyl 2-(3-nitro-5-(trifluoromethyl)pyridin-2-yl)malonate (320 mg, 0.993 mmol) was combined with aq HCl (3 M, 5 mL, 15.00 mmol) and the mixture was heated to reflux overnight. The reaction mixture was cooled to RT and poured into EtOAc. Aqueous NaOH (2 M, 10 mL, 20 mmol) was added and the organic layer was separated and washed with water and brine, dried (MgSO4) and concentrated in vacuo to provide 2-methyl-3-nitro-5-(trifluoromethyl)pyridine (53 mg, 9% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.19 (s, 1 H), 8.80 (s, 1 H), 2.82 (s, 3 H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. customthe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a4c706c5ef64ecc8f1bc3d3e4998841
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

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