Toluene → HCID 59859868, 화합물

HRID 1944555노트

반응식

HRID 1944555 반응식
C(O[C:4](=[O:17])[C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][CH:8]=1)C.[NH2:18][C:19]1[CH:20]=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2.C[Al](C)C.C1(C)C=CC=CC=1>ClCCCl.C(OCC)C.CO>[N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[C:19]([NH:18][C:4](=[O:17])[C:5]#[C:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]([CH3:14])([CH3:15])[CH3:16])=[CH:11][CH:12]=2)[CH:20]=1

참가 물질

8

반응물 4

HCID 1140TolueneHCID 113753-AminoquinolineHCID 11333698Ethyl 3-(4-tert-Butylphenyl)propiolateHCID 16682925Trimethylaluminum

생성물 1

HCID 59859868HCID 59859868, 화합물

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 887Methanol용매HCID 3283Diethyl Ether용매

실험 절차

A solution of (4-tert-butyl-phenyl)-propynoic acid ethyl ester (0.23 g, 1.0 mmol) and 3-aminoquinoline (0.144 g, 1.0 mmol) in 1,2-dichloroethane (15 mL) was treated with a 2N solution of trimethylaluminum in toluene (0.75 mL, 1.5 mmol). The resultant solution was stirred at room temperature for 15 minutes, then heated at reflux for 18 h. The solution was cooled and treated with methanol (0.50 mL). The product was preabsorbed onto silica gel and purified by flash chromatography, using a gradient of methanol in dichloromethane as the eluant. The product was isolated, after trituration in diethyl ether, as a colorless solid, 0.17 g (52%). MS: m/z 329.2 (MH+). 1HNMR (DMSO-d6): δ 1.31 (s, 9 H), 7.54-7.72 (m, 6 H), 7.97 (d, 1 H), 8.72 (d, 1 H), 8.96 (d, 1 H) and 11.3 (s, 1 H).

후처리

  1. temperatureheated
  2. temperatureat reflux for 18 h
  3. temperatureThe solution was cooled
  4. customThe product was preabsorbed onto silica gel
  5. custompurified by flash chromatography
  6. customThe product was isolated

출처 및 근거

ORD 기록
ord-9e4bdf28025f4464bccd7795c172fc72
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394828B2

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