Methanol → [2-(2-Amino-5-chlorophenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester

HRID 580380Notes

Reaction equation

HRID 580380 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:27]([O-])=O)=[C:6]([CH2:8][CH:9]([CH:18]([C:23]([O:25][CH3:26])=[O:24])[C:19]([O:21][CH3:22])=[O:20])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:7]=1.CO.O.[OH-].[NH4+]>C(OCC)(=O)C>[NH2:27][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=1[CH2:8][CH:9]([CH:18]([C:23]([O:25][CH3:26])=[O:24])[C:19]([O:21][CH3:22])=[O:20])[C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14923Ammonium HydroxideHCID 14156188HCID 14156188, compound

Product 1

HCID 14156189[2-(2-Amino-5-chlorophenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl esterYield 75.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a refluxing mixture of [2-(5-chloro-2-nitrophenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester (40 g, 95.0 mmole) and hydrated ferrous sulfate (184.5 g, 0.663 mole) in a (1:10 solution of methanol:water (1.2 L) was added concentrated ammonium hydroxide (142.5 ml) over a 30 minute period. The reaction was stirred at reflux for 20 minutes then cooled to room temperature. Ethyl acetate and Celite were added and the mixture was filtered through Celite. The filtrate was partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulfate and concentrated in vacuo. The product was recrystallized from isopropyl alcohol to yield 28.22 g of the title compound, melting point 114°-116° C.

Workup

  1. temperatureat reflux for 20 minutes
  2. filtrationthe mixture was filtered through Celite
  3. customThe filtrate was partitioned between ethyl acetate and water
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe product was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-d894818cfa0c4f2f99e9824df55fc176
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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