HCID 20303506, compound → 4-Amino-2,5-dichloro-α-methylbenzeneacetic acid

HRID 1733007Notes

Reaction equation

HRID 1733007 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([Cl:11])=[CH:4][C:3]=1[CH:12]([CH3:16])[C:13]([OH:15])=[O:14]>C(O)(=O)C.O.[Fe]>[NH2:8][C:6]1[C:5]([Cl:11])=[CH:4][C:3]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 1

HCID 20303506HCID 20303506, compound

Product 1

HCID 203035654-Amino-2,5-dichloro-α-methylbenzeneacetic acidYield 78.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

23 g (87 mmoles) of 2-(2,5-dichloro-4-nitrophenyl)propionic acid are heated to 95° C. in 100 ml of glacial acetic acid and 30 ml of water, and 14 g (0.25 mole) of iron powder are added in portions. After the exothermic reaction subsides, heating (to 95° C.) is effected for a further hour. Pouring onto 500 g of ice is effected, followed by extracting twice with, in each case, 200 ml of diethyl ether, washing the organic phase with water, drying, and concentrating in a vacuum to obtain 16 g (78.6% of theory) of 2-(4-amino-2,5-dichlorophenyl)propionic acid (m.p. 140° to 141° C.).

Workup

  1. customAfter the exothermic reaction subsides
  2. waitis effected for a further hour
  3. extractionby extracting twice with, in each case, 200 ml of diethyl ether
  4. washwashing the organic phase with water
  5. customdrying
  6. concentrationconcentrating in a vacuum

Sources & evidence

ORD record
ord-7ade05bc802145e1b10e5627d2c9638c
Source dataset
uspto-grants-1980_12
Patent number
US04239901

Reaction notes

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