Hydrochloric Acid → alpha-Ethyl-[2-(5-chloro-2-aminophenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester

HRID 580423Notes

Reaction equation

HRID 580423 reaction equation
[CH2:1]([C:3]([CH:12]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[CH2:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[N+:21]([O-])=O)([C:8]([O:10][CH3:11])=[O:9])[C:4]([O:6][CH3:7])=[O:5])[CH3:2].Cl.C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:1]([C:3]([CH:12]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[CH2:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[NH2:21])([C:8]([O:10][CH3:11])=[O:9])[C:4]([O:6][CH3:7])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate2×HCID 15128651Ethyl-[2-(5-chloro-2-nitrophenyl)-1-(4-methoxyphenyl) ethyl]propanedioic acid, dimethyl ester

Product 1

HCID 15128666alpha-Ethyl-[2-(5-chloro-2-aminophenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

α -Ethyl-[2-(5-chloro-2-nitrophenyl)-1-(4-methoxyphenyl) ethyl]propanedioic acid, dimethyl ester (12.64 g, 28.10 mmole) was dissolved in methanol (600 ml) under argon at room temperature. Powdered stannous chloride dihydrate (32.98 g, 146.2 mmole, 5.2 eq) was added followed by concentrated hydrochloric acid (36 ml) with stirring. The solution turned clear and homogeneous. After 2 hours, Celite, ethyl acetate and saturated potassium carbonate solution were added with stirring. (The potassium carbonate solution was added portionwise). The suspension was filtered though a pad of Celite and the Celite pad was rinsed with ethyl acetate (3 times). The filtrate was concentrated to remove most of the organic solvents, and the residue was collected by suction-filtration. The crude material was used without further purification.

Workup

  1. stirringwith stirring
  2. filtrationThe suspension was filtered though a pad of Celite
  3. washthe Celite pad was rinsed with ethyl acetate (3 times)
  4. concentrationThe filtrate was concentrated
  5. customto remove most of the organic solvents
  6. filtrationthe residue was collected by suction-filtration
  7. customThe crude material was used without further purification

Sources & evidence

ORD record
ord-7bcf863b8261481282a1d6e3d96fdc7c
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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