Hydrochloric Acid → 4-Hydrazinophenyl propionamide hydrochloride

HRID 128754Notes

Reaction equation

HRID 128754 reaction equation
[ClH:1].[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]([NH2:12])=[O:11])=[CH:5][CH:4]=1.[N:14]([O-])=O.[Na+]>O>[ClH:1].[NH:2]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH3:13])[C:10]([NH2:12])=[O:11])=[CH:7][CH:8]=1)[NH2:14]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 128052284-Aminophenyl propionamideHCID 23668193Sodium Nitrite

Product 1

HCID 189442744-Hydrazinophenyl propionamide hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated hydrochloric acid (4 ml) was added slowly, with cooling and stirring to 4-aminophenyl propionamide (0.80 g), maintaining the temperature below 5° C. To this slurry was added a solution of sodium nitrite (0.37 g) in water (2 ml), dropwise over 15 min, followed by stirring for a further 15 min. The turbid solution thus formed was added portionwise to a cooled, stirred solution of stannous chloride (2.19 g) in conclusion. HCl (4 ml), and the resulting mixture was stirred for 1 h. After filtering, the solution was reduced in volume until an inorganic precipitate formed. This was filtered off, and the filtrate was evaporated to dryness. The residual gum was crystallized from acetic acid to give crude 4-hydrazinophenyl propionamide hydrochloride (1.05 g).

Workup

  1. temperaturewith cooling
  2. temperaturemaintaining the temperature below 5° C
  3. customThe turbid solution thus formed
  4. additionwas added portionwise to a cooled
  5. filtrationAfter filtering
  6. customformed
  7. filtrationThis was filtered off
  8. customthe filtrate was evaporated to dryness
  9. customThe residual gum was crystallized from acetic acid

Sources & evidence

ORD record
ord-7e777d471a8c4d99958272ce872f866e
Source dataset
uspto-grants-1995_11
Patent number
US05464864

Reaction notes

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