ethyl N-(2,3-dichloro-6-nitrobenzyl)glycine hydrochloride → ethyl-N-(6-amino-2,3-dichlorobenzyl)glycine

HRID 481142

反応式

HRID 481142 の反応式
Cl.[CH2:2]([N:4]([CH2:9][C:10]1[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[C:12]([Cl:19])[C:11]=1[Cl:20])[CH2:5][C:6]([OH:8])=[O:7])[CH3:3]>O.C(O)C.[Pt]>[CH2:2]([N:4]([CH2:9][C:10]1[C:15]([NH2:16])=[CH:14][CH:13]=[C:12]([Cl:19])[C:11]=1[Cl:20])[CH2:5][C:6]([OH:8])=[O:7])[CH3:3]

参加物

5

反応物 1

HCID 66640009ethyl N-(2,3-dichloro-6-nitrobenzyl)glycine hydrochloride2 回

生成物 1

HCID 67080112ethyl-N-(6-amino-2,3-dichlorobenzyl)glycine収率 72%

試薬・触媒・溶媒 3

HCID 23939Platinum触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A solution of 0.344 g of ethyl N-(2,3-dichloro-6-nitrobenzyl)glycine hydrochloride (compound VI) in 1.5 mL of water and 1.5 mL ethanol (with 5% isopropanol) was stirred and 5% sulfided platinum on carbon under hydrogen (50 to 100 psi) for 16 hours. The catalyst was removed by filtration. The filtrate concentrated, diluted with water and toluene, and basified (aqueous sodium hydroxide or potassium carbonate) to pH 9-10. The organic phase was separated, concentrated, and the crude material purified by low-temperature recrystallization from toluene in hexane to give compound I in 72% yield.

後処理

  1. customThe catalyst was removed by filtration
  2. concentrationThe filtrate concentrated
  3. additiondiluted with water and toluene, and basified (aqueous sodium hydroxide or potassium carbonate) to pH 9-10
  4. customThe organic phase was separated
  5. concentrationconcentrated
  6. customthe crude material purified by low-temperature recrystallization from toluene in hexane

出典と根拠

ORDレコード
ord-5ecaf55e573e49b5b990f95c786a5cfc
出典データセット
uspto-grants-2003_11
特許番号
US06653500B2

関連ノート

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