Perchloric Acid → (RS)-2-(n-pentadecyl)indoline-5-carboxylic acid hydrochloride

HRID 2412616노트

반응식

HRID 2412616 반응식
[Cl:1](O)(=O)(=O)=O.[CH2:6]([C:21]1[NH:22][C:23]2[C:28]([CH:29]=1)=[CH:27][C:26]([C:30]([OH:32])=[O:31])=[CH:25][CH:24]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>C(O)(=O)C.[Pd]>[ClH:1].[CH2:6]([CH:21]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:30]([OH:32])=[O:31])[CH:27]=2)[NH:22]1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

참가 물질

5

반응물 2

HCID 24247Perchloric AcidHCID 127972172-(n-Pentadecyl)indole-5-carboxylic acid

생성물 1

HCID 24839535(RS)-2-(n-pentadecyl)indoline-5-carboxylic acid hydrochloride

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

Perchloric acid (3 ml) was added to a hot solution of 2-(n-pentadecyl)indole-5-carboxylic acid in glacial acetic acid (60 ml) and the mixture was hydrogenated at normal pressure using palladium on charcoal (5% w/w, 0.7 g) as catalyst. After 3.5 hours the hot mixture was filtered and the residue was washed with hot glacial acetic acid (30 ml). The pH of the combined filtrates was adjusted to 6 with 10% w/v sodium hydroxide solution. The mixture was extracted with diethyl ether (2×75 ml) and the ether solution was dried over magnesium sulphate. The solution was treated with a saturated solution of hydrogen chloride gas in ethanol to precipitate the hydrochloride. The solid was collected and recrystallised from isopropanol to give (RS)-2-(n-pentadecyl)indoline-5-carboxylic acid hydrochloride (5.6 g) as a white solid, m.p. 165°-170° C. with decomposition.

후처리

  1. filtrationAfter 3.5 hours the hot mixture was filtered
  2. washthe residue was washed with hot glacial acetic acid (30 ml)
  3. extractionThe mixture was extracted with diethyl ether (2×75 ml)
  4. dry with materialthe ether solution was dried over magnesium sulphate
  5. additionThe solution was treated with a saturated solution of hydrogen chloride gas in ethanol
  6. customto precipitate the hydrochloride
  7. customThe solid was collected
  8. customrecrystallised from isopropanol

출처 및 근거

ORD 기록
ord-41012679da644559bc5795a614dd1b46
출처 데이터셋
uspto-grants-1985_01
특허 번호
US04493843

반응 노트

불러오는 중…