Ethyl orthoformate → 4-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline

HRID 1450693Notes

Reaction equation

HRID 1450693 reaction equation
[Cl:1][C:2]1[C:11]([NH2:12])=[C:10]([NH:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:18](OC(OCC)OCC)C>C(O)C>[Cl:1][C:2]1[C:11]2[N:12]=[CH:18][N:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 117470392-Chloro-N~4~-(2-methylpropyl)quinoline-3,4-diamine

Product 1

HCID 3839614-chloro-1-isobutyl-1H-imidazo[4,5-c]quinolineYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2-chloro-N4 -(2-methylpropyl)-3,4-quinolinediamine (35 g) and triethylorthoformate (52.3 g, 2.5 eq) was heated at 145° C. for 10 h, during which time ethanol was removed by distillation. The resulting mixture was cooled to room temperature and the solid was removed by filtration. The solid was dissolved in hydrochloric acid (100 mL, 4N). The resulting solution was added to a solution of sodium hydroxide. The precipitate was filtered and washed with water to afford the product 4-chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline in 92% yield.

Workup

  1. customwas removed by distillation
  2. customthe solid was removed by filtration
  3. dissolutionThe solid was dissolved in hydrochloric acid (100 mL, 4N)
  4. additionThe resulting solution was added to a solution of sodium hydroxide
  5. filtrationThe precipitate was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-79808bf169e845149fa6b75eb8a65d06
Source dataset
uspto-grants-1997_02
Patent number
US05602256

Reaction notes

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