Toluene → HCID 59859868, compound

HRID 1944555Notes

Reaction equation

HRID 1944555 reaction equation
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

Participants

8

Reactant 4

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

Product 1

HCID 59859868HCID 59859868, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-9e4bdf28025f4464bccd7795c172fc72
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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