Ethanol → 2-Cyano-5-ethoxalylaminobenzotrifluoride

HRID 346131Notes

Reaction equation

HRID 346131 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13])#[N:2].C(N(CC)CC)C.[CH2:23]([OH:25])[CH3:24].[OH2:26].[CH2:27]([OH:29])[CH3:28]>[Pd].O1CCCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:23]([C:24]([O:29][CH2:27][CH3:28])=[O:26])=[O:25])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13])#[N:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 27757834-Nitro-2-(trifluoromethyl)benzonitrileHCID 19096565Water ethanol

Product 1

HCID 199904272-Cyano-5-ethoxalylaminobenzotrifluorideYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.8 g (31.5 mmol) 2-cyano-5-nitrobenzotrifluoride in 200 ml ethanol was hydrogenated at atm. pressure by using 0.4 g 5% Pd-C as a catalyst. The reaction mixture was filtered and evaporated in vacuo. The crude product was dissolved in 150 ml dry tetrahydrofuran and added 6.0 ml (43.6 mmol) dry triethylamine. A solution of 4.4 ml (39.4 mmol) ethyl oxalylchlorid in 30 ml dry tetrahydrofuran was added dropwise, and then stirring was continued at 25° C. for 3 h. The filtered and evaporated reaction product was stirred with ethanol-water to give 7.3 g (82%) of 2-cyano-5-ethoxalylaminobenzotrifluoride. M.p. 112-114° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated in vacuo
  3. dissolutionThe crude product was dissolved in 150 ml dry tetrahydrofuran
  4. filtrationThe filtered
  5. customevaporated
  6. customreaction product

Sources & evidence

ORD record
ord-136b25eaf47b45ad89aa0d4d45324668
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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