Hydrochloric Acid → Ethyl 4-aminomethylsalicylate hydrochloride

HRID 985168노트

반응식

HRID 985168 반응식
[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

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 22556088Ethyl 4-azidomethylsalicylateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 12794728Ethyl 4-aminomethylsalicylate hydrochloride수율 71%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-19b7df73ca2247a986aff510f2002641
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06870065B2

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