Ethyl orthopropionate → 1-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

HRID 258245Notes

Reaction equation

HRID 258245 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:18](OCC)(OCC)(OCC)[CH2:19][CH3:20]>C(OCC)(=O)C.CCOCC>[CH3:15][C:14]([CH3:17])([OH:16])[CH2:13][N:12]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[C:18]1[CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 66995Ethyl orthopropionateHCID 149869411-((3-Aminoquinolin-4-yl)amino)-2-methylpropan-2-ol

Product 1

HCID 197373151-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-olYield 84.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture containing 15.4 g (0.067 mol) of 1-[(3-amino-4-quinolinyl)amino]-2-methyl-2-propanol (U.S. Pat. No. 4,689,338 example 189) and 14.5 mL (0.07 mol) of triethyl orthopropionate was heated at about 165° C. for about 2 hours. The resulting solid was slurried in a mixture of ethyl acetate and ether, collected and dried to provide 15.2 g of a solid. This material was used without further purification.

Workup

  1. customcollected
  2. customdried

Sources & evidence

ORD record
ord-e9d81d33a9e24fa3a83a73ec3d2add9b
Source dataset
uspto-grants-1993_11
Patent number
US05266575

Reaction notes

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