Ammonium formate → HCID 43115453, compound

HRID 875181Notes

Reaction equation

HRID 875181 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][C:12]([F:15])([F:14])[F:13])([O-])=O.C([O-])=O.[NH4+]>C1COCC1.CO>[F:13][C:12]([F:14])([F:15])[CH2:11][NH:10][C:5]1[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 19784794HCID 19784794, compound

Product 1

HCID 43115453HCID 43115453, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-nitro-phenyl)-(2,2,2-trifluoro-ethyl)-amin (2.16 g, 9.8 mmol) in THF (6 mL) and MeOH (24 mL) at 0° C. was added ammonium formate (2.47 g, 39.2 mmol). The resulting mixture was purged with nitrogen, then 10% Pd/C (57 mg) was added. The ice bath was removed and the reaction mixture was stirred at room temperature for 5 h. The resulting mixture was filtered over CELITE®, washing with EtOAc. Removal of the solvent in vacuo yield N-(2,2,2-trifluoro-ethyl)-benzene-1,2-diamine, which was used in the next step without further purification. MS 191 (M+1)+.

Workup

  1. customThe resulting mixture was purged with nitrogen
  2. addition10% Pd/C (57 mg) was added
  3. customThe ice bath was removed
  4. filtrationThe resulting mixture was filtered over CELITE®
  5. washwashing with EtOAc
  6. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-e207f0cfe68846b88b73e207c79fdad2
Source dataset
uspto-grants-2015_03
Patent number
US08981113B2

Reaction notes

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