Methanol → HCID 59529863, compound

HRID 1410261Notes

Reaction equation

HRID 1410261 reaction equation
B.[N+:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[C:14]([F:17])([F:16])[F:15])[C:8]([NH2:10])=O)([O-:4])=[O:3].CO>C1COCC1>[N+:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[C:14]([F:15])([F:16])[F:17])[CH2:8][NH2:10])([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 595298513-Nitro-4-(trifluoromethyl)benzamide

Product 1

HCID 59529863HCID 59529863, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1 M solution of Borane in THF (51 ml, 51 mmol) was added at 0° C. to 3-nitro-4-trifluoromethyl-benzoic acid amide (3.00 g, 12.8 mmol) in 50 ml THF and it was stirred for 3 days. Methanol was carefully added and it was stirred for 30 min at r.t and 2 h at reflux. Then it was concentrated i.vac.; NaOH was added (pH 8) and the mixture was extracted with EtOAc. The organic layer was dried with Na2SO4, filtered and concentrated to furnish the crude subtitle compound.

Workup

  1. stirringit was stirred for 30 min at r.t and 2 h
  2. temperatureat reflux
  3. concentrationThen it was concentrated i.vac
  4. additionNaOH was added (pH 8)
  5. extractionthe mixture was extracted with EtOAc
  6. dry with materialThe organic layer was dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-580318d841464a61a20397f9b11db26e
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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