Hexane → alpha-Amino-9H-xanthene-9-acetic acid hydrochloride

HRID 2399623노트

반응식

HRID 2399623 반응식
[ClH:1].[NH2:2][CH:3]([CH:9]1[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:16][C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:4]([O:6]CC)=[O:5].[OH-].[K+].CCCCCC>O.C(O)C.C(O)(=O)C.CC(O)C>[ClH:1].[NH2:2][CH:3]([CH:9]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[O:16][C:17]2[C:22]1=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:4]([OH:6])=[O:5]

참가 물질

8

반응물 3

HCID 8058HexaneHCID 14797Potassium Hydroxide2회HCID 67803757Ethyl alpha-amino-9H-xanthene-9-acetate hydrochloride

생성물 1

HCID 67805111alpha-Amino-9H-xanthene-9-acetic acid hydrochloride

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 702Ethanol용매2회HCID 962Water용매HCID 3776Isopropanol용매

실험 절차

Ethyl α-amino-9H-xanthene-9-acetate hydrochloride (5.33 g, 17 mmol) is combined with 45 mL of absolute ethanol and 27 mL of 1.25M ethanolic potassium hydroxide solution (2 equivalents). The progress of the reaction is monitored by thin layer chromatography (TLC), silica gel (SiO2), hexane:2-propanol/3:7 with 1% of acetic acid. After 13 hours and an additional two equivalents of the potassium hydroxide solution (in three portions) most of the starting material is consumed. Ethanol is stripped off, the residue is taken up in 100 mL of water, and extracted with diethyl ether. The aqueous portion is acidified with 0.5N hydrochloric acid (~100 mL) to pH 2 and cooled overnight. A white precipitate is collected by filtration, washed with cold water, diethyl ether, and dried at 50° C./10 mm Hg. This provides 3.18 g of the title compound; mp 264°-269° C. (dec).

후처리

  1. extractionextracted with diethyl ether
  2. temperaturecooled overnight
  3. filtrationA white precipitate is collected by filtration
  4. washwashed with cold water, diethyl ether
  5. customdried at 50° C./10 mm Hg

출처 및 근거

ORD 기록
ord-f95bebc8a6e14ae69d7db001f21c455d
출처 데이터셋
uspto-grants-1995_09
특허 번호
US05449778

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