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

HRID 580380ノート

反応式

HRID 580380 の反応式
[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

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 14923Ammonium HydroxideHCID 14156188HCID 14156188、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d894818cfa0c4f2f99e9824df55fc176
出典データセット
uspto-grants-1988_06
特許番号
US04752645

反応ノート

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