Toluene → HCID 45119472, compound

HRID 2243464Notes

Reaction equation

HRID 2243464 reaction equation
Cl[CH2:2]Cl.[C:4](Cl)(=[O:6])[CH3:5].[CH:8]([N:11](CC)C(C)C)(C)[CH3:9].[H-].[Na+].[C:19]1([CH3:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(OC(=O)C)(=O)C.C(N(CC)CC)C.N1C=CC=CC=1.O1CCCC1>[C:4]([N:11]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:25]([CH3:2])=[CH:9][CH2:8]1)(=[O:6])[CH3:5]

Participants

10

Reactant 5

HCID 1140TolueneHCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 81531Diisopropylethylamine

Product 1

HCID 45119472HCID 45119472, compound

Reagents, catalysts & solvents 4

HCID 1049PyridineSolventHCID 7918Acetic AnhydrideSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

Subsequent 1-N-acetylation of the compounds of formula III-a-b can be carried out using standard conditions. In a typical experiment, compounds of formula III-a-b are heated under reflux in acetic anhydride or reacted in a solvent such as dichloromethane, tetrahydrofuran, toluene or pyridine with acetyl chloride in the presence of a base such as N,N-diisopropylethylamine, triethylamine or sodium hydride to give the 1-N-acetyl-4-methyl-1,2-dihydroquinoline derivatives of formula IV-a-b.

Workup

  1. temperatureIn a typical experiment, compounds of formula III-a-b are heated

Sources & evidence

ORD record
ord-f80714434d4a4d9aacad3d5890ca3fc6
Source dataset
uspto-grants-2010_03
Patent number
US07674909B2

Reaction notes

Loading…