Ammonium Chloride → 4-Ethynyl-3-aminobenzamide

HRID 1844789Notes

Reaction equation

HRID 1844789 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-])=O)#[CH:2].[Cl-].[NH4+]>[Fe].O1CCCC1>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][C:4]=1[NH2:12])#[CH:2]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 569623664-Ethynyl-3-nitrobenzamide

Product 1

HCID 866947874-Ethynyl-3-aminobenzamideYield 59.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5 g (26.3 mmol) 4-Ethynyl-3-nitrobenzamide (Compound XII-1) and 75 ml tetrahydrofuran were added into a 150 ml four-necked flask, mechanically stirred to dissolve, and added with 10 ml aqueous solution of 10 g (186.9 mmol) ammonium chloride, then 10 g (178.5 mmol) iron powder was added portionwise and reacted at room temperature for 4 hours until the reaction was completed. The mixture was filtrated, and the filter cake was washed with tetrahydrofuran. The filtrate was extracted with ethyl acetate and the organic phase was washed with water, dried over anhydrous sodium sulfate, decolorized with activated charcoal, filtered, and concentrated to precipitate a solid, which was filtrated and dried to obtain 4-ethynyl-3-aminobenzamide (Compound XI-1, gray solid), 2.4 g, yield 59.4%.

Workup

  1. dissolutionto dissolve
  2. customreacted at room temperature for 4 hours until the reaction
  3. filtrationThe mixture was filtrated
  4. washthe filter cake was washed with tetrahydrofuran
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washthe organic phase was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto precipitate a solid, which
  11. filtrationwas filtrated
  12. customdried

Sources & evidence

ORD record
ord-b211c6953d1c4623b613919bcf432981
Source dataset
uspto-grants-2015_02
Patent number
US08946478B2

Reaction notes

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