Potassium Carbonate → 2-Chloro-3-nitro-6-trifluoromethyl-pyridin-4-ylamine

HRID 639628Notes

Reaction equation

HRID 639628 reaction equation
C([NH:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:12]=[C:11]([Cl:19])[C:10]=1[N+:20]([O-:22])=[O:21])C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>S(=O)(=O)(O)O>[Cl:19][C:11]1[C:10]([N+:20]([O-:22])=[O:21])=[C:9]([NH2:8])[CH:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[N:12]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86614472Benzyl-(2-chloro-3-nitro-6-trifluoromethyl-pyridin-4-yl)-amine

Product 1

HCID 866144742-Chloro-3-nitro-6-trifluoromethyl-pyridin-4-ylamineYield 97.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Benzyl-(2-chloro-3-nitro-6-trifluoromethyl-pyridin-4-yl)-amine (3.1 g, 9.3 mmol) was stirred in 5 ml concentrated sulphuric acid for 0.5 h before cautiously pouring the solution into a beaker of crushed ice. Solid K2CO3 was added portion-wise until a basic pH was achieved and the aqueous extracted with 2×50 ml EtOAc. The combined organics were dried over MgSO4 and concentrated in vacuo to afford 2.2 g of the title compound as a pale yellow solid.

Workup

  1. additionbefore cautiously pouring the solution into a beaker of crushed ice
  2. extractionthe aqueous extracted with 2×50 ml EtOAc
  3. dry with materialThe combined organics were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d0f975d55a64453ba65a58f07ff882d
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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