Hydrochloric Acid → HCID 21075713, compound

HRID 1373943Notes

Reaction equation

HRID 1373943 reaction equation
[N:1]1([NH:14]C(=O)OC(C)(C)C)[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.Cl>C(O)C.C(OCC)C>[N:1]1([NH2:14])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21075817HCID 21075817, compound

Product 1

HCID 21075713HCID 21075713, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of tert-butyl N-(1H-imidazo[4,5-c]quinolin-1-yl)carbamate (6.74 g, 23.7 mmol) in 40 mL of ethanol was treated with 40 mL of HCl (40 mL, 119 mmol, 3 M in ethanol) and heated to reflux. After 1 h, the reaction mixture was cooled to ambient temperature, diluted with 80 mL of diethyl ether, and cooled in an ice water bath which precipitated a tan solid. The HCl salt of the product was collected by vacuum filtration and rinsed with diethyl ether until the filtrate ran clear. The dried HCl salt was dissolved in 75 mL of water and made basic by addition of 50% NaOH solution until the pH of the water was 12–13. The free base of the product precipitated out and was triturated in the basic water for 30 min while being cooled in an ice water bath. The solid was collected by vacuum filtration and dried under vacuum to give 2.86 g of 1H-imidazo[4,5-c]quinolin-1-amine as a tan granular solid.

Workup

  1. temperatureheated to reflux
  2. temperaturecooled in an ice water bath which
  3. customprecipitated a tan solid
  4. filtrationThe HCl salt of the product was collected by vacuum filtration
  5. washrinsed with diethyl ether until the filtrate
  6. dissolutionThe dried HCl salt was dissolved in 75 mL of water
  7. additionmade basic by addition of 50% NaOH solution until the pH of the water
  8. customThe free base of the product precipitated out
  9. customwas triturated in the basic water for 30 min
  10. temperaturewhile being cooled in an ice water bath
  11. filtrationThe solid was collected by vacuum filtration
  12. customdried under vacuum

Sources & evidence

ORD record
ord-c1da8ca20c2f4a10b6fea74a8dfa4b93
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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