Hydrochloric Acid → 2-Benzylamino-3-nitro-5-trifluoromethyl-benzoic acid

HRID 1910213Notes

Reaction equation

HRID 1910213 reaction equation
Cl[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14]([F:17])([F:16])[F:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>CN(C=O)C>[CH2:18]([NH:25][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14]([F:17])([F:16])[F:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 100844572-chloro-3-nitro-5-(trifluoromethyl)benzoic Acid

Product 1

HCID 669407092-Benzylamino-3-nitro-5-trifluoromethyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring solution of 0.81 g (3.0 mmol) of the above 2-chloro-3-nitro-5-trifluoromethyl-benzoic acid in 6.0 mL of DMF was added 6.0 mL of TEA, followed by 3.0 mmol of Benzylamine. The mixture was heated at 80° C. for 6 h. After cooling to r.t., 3.0 mL of 6N HCl solution was added. The solid was collected, washed with fresh water to give 2-benzylamino-3-nitro-5-trifluoromethyl-benzoic acid. LCMS: 341 (M+1)+. This product was hydrogenated according to the general procedure C to give 0.25 g of 2,3-diamino-5-trifluoromethyl-benzoic acid. LCMS: 221 (M+1)+.

Workup

  1. temperatureAfter cooling to r.t.
  2. customThe solid was collected
  3. washwashed with fresh water

Sources & evidence

ORD record
ord-b2798a96a35d4d54b49a831ebf757719
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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