2-tert-Butylaniline → HCID 57465584, compound

HRID 1042992Notes

Reaction equation

HRID 1042992 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:14]3[C:15]([CH3:20])=[N:16][O:17][C:18]=3[CH3:19])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22].[C:26]([C:30]1[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=1[NH2:32])([CH3:29])([CH3:28])[CH3:27]>O1CCOCC1>[CH3:29][C:26]([C:30]1[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=1[NH:32][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:14]3[C:15]([CH3:20])=[N:16][O:17][C:18]=3[CH3:19])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 805742-tert-ButylanilineHCID 57465583HCID 57465583, compound2×

Product 1

HCID 57465584HCID 57465584, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methoxy)-3-quinolinecarboxylate (for a preparation see Intermediate 42 (3.3 g, 9.2 mmol) and 2-tert-butylaniline (2.7 ml, 18.4 mmol) in dioxane (50 ml) was refluxed for 2 days. After cooling, the reaction mixture was evaporated under reduced pressure and the precipitate was purified by chromatography on silica gel eluting with DCM/MeOH (95/5) to give the title compound as a solid (1.2 g, 27.7%).

Workup

  1. temperaturewas refluxed for 2 days
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated under reduced pressure
  4. customthe precipitate was purified by chromatography on silica gel eluting with DCM/MeOH (95/5)

Sources & evidence

ORD record
ord-0df97b2a8949440db564c348351fe8e1
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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