Hydrochloric Acid → 7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-amine

HRID 1373959Notes

Reaction equation

HRID 1373959 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([NH:22]C(=O)OC(C)(C)C)[C:20]([CH2:30][O:31][CH2:32][CH3:33])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([NH2:22])[C:20]([CH2:30][O:31][CH2:32][CH3:33])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86596852HCID 86596852, compound

Product 1

HCID 210757477-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-amineYield 61.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
100 °C

Procedure

A suspension of tert-butyl (7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)carbamate (14.4 g, 32.1 mmol) in 100 mL of ethanol was treated with HCl in ethanol (38 mL, 160 mmol, 4.3 M). The mixture was heated to 100° C. under an atmosphere of nitrogen. After 2 h, the reaction mixture was cooled to ambient temperature at which point a solid precipitated from solution. The mixture was diluted with 100 mL of diethyl ether and the solid was triturated for 15 min. The solid was collected by vacuum filtration and washed with several portions of diethyl ether. The solid was dried under vacuum for 2 h. The dry solid was suspended in 150 mL of water and treated with 50% NaOH solution until the pH of the liquid was 12. A brown solid precipitated. The mixture was diluted with 200 mL of CH2Cl2 and stirred until the solid dissolved. The layers were then separated. The aqueous portion was extracted with CH2Cl2 (2×100 mL). The combined organic extracts were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield 6.91 g of 7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-amine as a dark tan solid.

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature at which point a solid
  2. customprecipitated from solution
  3. additionThe mixture was diluted with 100 mL of diethyl ether
  4. customthe solid was triturated for 15 min
  5. filtrationThe solid was collected by vacuum filtration
  6. washwashed with several portions of diethyl ether
  7. customThe solid was dried under vacuum for 2 h
  8. additiontreated with 50% NaOH solution until the pH of the liquid
  9. customA brown solid precipitated
  10. additionThe mixture was diluted with 200 mL of CH2Cl2
  11. dissolutiondissolved
  12. customThe layers were then separated
  13. extractionThe aqueous portion was extracted with CH2Cl2 (2×100 mL)
  14. washThe combined organic extracts were washed with brine (100 mL)
  15. dry with materialdried over Na2SO4
  16. filtrationfiltered
  17. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c484bd6ef5044d8ca94ec7603299760c
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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