Hydrochloric Acid → Ethyl 4-aminomethylsalicylate hydrochloride

HRID 985168ノート

反応式

HRID 985168 の反応式
[N:1]([CH2:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([OH:16])[CH:6]=1)=[N+]=[N-].[ClH:17].[H][H]>[Pd].C(O)C>[ClH:17].[NH2:1][CH2:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([OH:16])[CH:6]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 22556088Ethyl 4-azidomethylsalicylateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 12794728Ethyl 4-aminomethylsalicylate hydrochloride収率 71%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

Palladium on carbon (0.5 g; 10% [w/w]) was added to a 1 L hydrogenation flask under a nitrogen atmosphere. The crude ethyl 4-azidomethyl-2-hydroxybenzoate was dissolved in ethanol (200 mL) and transferred to the hydrogenation flask. Concentrated aqueous hydrochloric acid (2 mL) was then added, and the flask was affixed to the Parr hydrogenator. The reaction mixture was shaken under 35 psi of hydrogen for 4 hours at room temperature. The mixture was then filtered through Celite to remove the catalyst, and the filtrate was evaporated to dryness to afford an off-white solid. Finally, this solid was crystallized from EtOH to afford 3.1 g (71% yield) of ethyl 4-(aminomethyl)-2-hydroxybenzoate hydrochloride (m.p. 240-241° C.).

後処理

  1. filtrationThe mixture was then filtered through Celite
  2. customto remove the catalyst
  3. customthe filtrate was evaporated to dryness
  4. customto afford an off-white solid
  5. customFinally, this solid was crystallized from EtOH

出典と根拠

ORDレコード
ord-19b7df73ca2247a986aff510f2002641
出典データセット
uspto-grants-2005_03
特許番号
US06870065B2

反応ノート

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