Pyridine → Benzamide, 4-nitro-N-2-propynyl-

HRID 880488Notes

Reaction equation

HRID 880488 reaction equation
Cl.[CH2:2]([NH2:5])[C:3]#[CH:4].N1C=CC=CC=1.[N+:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)([O-:14])=[O:13]>O1CCCC1>[N+:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:5][CH2:2][C:3]#[CH:4])=[O:20])=[CH:17][CH:16]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 85024-Nitrobenzoyl chlorideHCID 11205720Prop-2-ynylamine hydrochloride

Product 1

HCID 3016782Benzamide, 4-nitro-N-2-propynyl-Yield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of propargylamine hydrochloride (5.0 g, 54.6 mmol) and pyridine (7.8 g, 99.1 mmol) in tetrahydrofuran (30 mL) was added 4-nitro-benzoylchloride (9.2 g, 49.6 mmol) in tetrahydrofuran (20 mL) and the mixture was heated at reflux for 16 h. The mixture was allowed to cool to ambient temperature and concentrated in vacuo. The crude residue was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution, water, brine, dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to afford 4-nitro-N-prop-2-ynyl-benzamide (7.74 g, 77%) as a solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude residue was dissolved in ethyl acetate
  5. washwashed with saturated aqueous sodium bicarbonate solution, water, brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82444f68bda74462823d049127359f81
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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