Ethyl orthoformate → HCID 22320486, compound

HRID 521262Notes

Reaction equation

HRID 521262 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][C:15]=1[NH2:24])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:25](OCC)(OCC)OCC>C1(C)C=CC=CC=1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:24]=[CH:25]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 12106183HCID 12106183, compound

Product 1

HCID 22320486HCID 22320486, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N4-[4-(tert-butyldimethylsilanyloxy)butyl]quinoline-3,4-diamine (101 g, 293 mmol) and triethyl orthoformate (43.4 g, 293 mmol) in toluene (200 mL) was heated at reflux for 2 hours and then concentrated under reduced pressure to provide 1-[4-(tert-butyldimethylsilanyloxy)butyl]-1H-imidazo[4,5-c]quinoline as an oil that was used directly in the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-220d698cdd544e2ca5a1bee341c54e3b
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

Loading…