Ammonia → 4-Ethynyl-3-nitrobenzamide

HRID 1844781Notes

Reaction equation

HRID 1844781 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14])#[CH:2].CO.[NH3:18]>O1CCCC1>[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH2:18])=[O:8])=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14])#[CH:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86694785Methyl 4-ethynyl-3-nitrobenzoate

Product 1

HCID 569623664-Ethynyl-3-nitrobenzamideYield 53.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.3 g (0.036 mol) Methyl 4-ethynyl-3-nitrobenzoate (Compound II-1), 300 ml methanol and 200 ml tetrahydrofuran were added into a reaction flask, stirred, and ammonia gas was passed through for 1 hour. Then the mixture was reacted at room temperature for 24 hours. After completion of the reaction monitored by TLC, the mixture was concentrated under reduced pressure with most of the tetrahydrofuran and methanol evaporated, then extracted with 300 ml ethyl acetate. The organic layer was washed with water for three times, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness, and separated by column chromatography to obtain 4-ethynyl-3-nitrobenzamide (compound I-1), 3.6 g (0.0019 mol), yield 53.2%.

Workup

  1. customwas passed through for 1 hour
  2. customThen the mixture was reacted at room temperature for 24 hours
  3. concentrationthe mixture was concentrated under reduced pressure with most of the tetrahydrofuran and methanol
  4. customevaporated
  5. extractionextracted with 300 ml ethyl acetate
  6. washThe organic layer was washed with water for three times
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated to dryness
  10. customseparated by column chromatography

Sources & evidence

ORD record
ord-c829cf25f5a9463fa7b78dc4feee3ba8
Source dataset
uspto-grants-2015_02
Patent number
US08946478B2

Reaction notes

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