Hydrazine hydrate (1:1) → 3-Amino-α-methylbenzeneacetic acid

HRID 1449241Notes

Reaction equation

HRID 1449241 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[N+:13]([O-])=O.O.NN>C(O)C.[Pd]>[NH2:13][C:3]1[CH:4]=[C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:6]=[CH:7][CH:2]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 11064234HCID 11064234, compound

Product 1

HCID 108447663-Amino-α-methylbenzeneacetic acidYield 90.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

To a mixture of 4.6 g of 2-(4-chloro-3-nitrophenyl) propionic acid and 250 mg of 10% palladium-on-charcoal in 50 ml of ethanol, was added dropwise 2.5 g of hydrazine hydrate under a stream of nitrogen. After the completion of the addition, the mixture was stirred at room temperature for one hour and then refluxed for 6 hours. The resulting mixture was cooled to room temperature, mixed with 250 mg of 10% palladium-on-charcoal and 2.5 g of hydrazine hydrate, and refluxed for 6 hours. After filtration, the filtrate was evaporated and dissolved in 20 ml of water. The aqueous solution was adjusted to pH 5-6 with 6 N hydrochloric acid and then concentrated to a volume of 20 ml. On standing overnight at room temperature, 3.0 g of 2-(m-aminophenyl)propionic acid was obtained; m.p. 98°-100° C.; Analysis--Calculated for C9H11NO2 : C 65.43%, H 6.71%, N 8.48%, Found C 65.41%, H 6.72%, N 8.48%.

Workup

  1. additionAfter the completion of the addition
  2. temperaturerefluxed for 6 hours
  3. temperatureThe resulting mixture was cooled to room temperature
  4. temperaturerefluxed for 6 hours
  5. filtrationAfter filtration
  6. customthe filtrate was evaporated
  7. dissolutiondissolved in 20 ml of water
  8. concentrationconcentrated to a volume of 20 ml
  9. waitOn standing overnight at room temperature

Sources & evidence

ORD record
ord-4d66794044ec4a218dc5e9a53e2ea058
Source dataset
uspto-grants-1980_02
Patent number
US04189607

Reaction notes

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