Ethyl orthoformate → HCID 13958485, compound

HRID 255558Notes

Reaction equation

HRID 255558 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH:14]([OH:16])[CH3:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH:17](OCC)(OCC)OCC>C(O)=O>[OH:16][CH:14]([CH3:15])[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]=[CH:17]1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 20183599HCID 20183599, compound

Product 1

HCID 13958485HCID 13958485, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidCatalyst

Conditions

Temperature
150 °C

Procedure

A mixture of 32.9 g of 3-amino-4-(2-hydroxypropylamino)quinoline in 100 ml of triethyl orthoformate and 10 drops of formic acid was heated at 150° C. for two hours. The mixture was evaporated under vacuum, then 200 ml of water was added and the pH was adjusted to pH 2 to 3 with concentrated hydrochloric acid. The solution was basified with ammonium hydroxide, then with 50 percent sodium hydroxide solution. An oily product eventually solidified and was separated by filtration. Recrystallization from a mixture of hexane and dichloromethane gave an off-white solid 1-(2-hydroxypropyl)-1H-imidazo[4,5-c]quinoline, m.p. 171° C.

Workup

  1. customThe mixture was evaporated under vacuum
  2. addition200 ml of water was added
  3. customwas separated by filtration
  4. customRecrystallization
  5. additionfrom a mixture of hexane and dichloromethane

Sources & evidence

ORD record
ord-e8737213fac742fc98208439bbd0be8a
Source dataset
uspto-grants-1987_10
Patent number
US04698348

Reaction notes

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