Hydrochloric Acid → HCID 21075721, compound

HRID 1373937Notes

Reaction equation

HRID 1373937 reaction equation
[CH2:1]([C:4]1[N:5]([NH:17]C(=O)OC(C)(C)C)[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].Cl>C(O)C.C(OCC)C>[CH2:1]([C:4]1[N:5]([NH2:17])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86594229HCID 86594229, compound

Product 1

HCID 21075721HCID 21075721, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of tert-butyl (2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)carbamate (7.23 g, 22.2 mmol) in 40 mL of ethanol was treated with HCl (37 mL, 111 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. 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 treated with 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 4.64 g of 2-propyl-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
  3. filtrationThe HCl salt of the product was collected by vacuum filtration
  4. washrinsed with diethyl ether until the filtrate
  5. dissolutionThe dried HCl salt was dissolved in 75 mL of water
  6. additiontreated with 50% NaOH solution until the pH of the water
  7. customThe free base of the product precipitated out
  8. customwas triturated in the basic water for 30 min
  9. temperaturewhile being cooled in an ice water bath
  10. filtrationThe solid was collected by vacuum filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-a05caef6bfa14ae7b42f03f6c1b5efa0
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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