Hydrochloric Acid → 2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethylamine

HRID 598364Notes

Reaction equation

HRID 598364 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]2[C:14]3[N:22]([CH2:23][C:24]([NH:27]C(=O)OC(C)(C)C)([CH3:26])[CH3:25])[C:21]([CH2:35][O:36][CH2:37][CH3:38])=[N:20][C:15]=3[CH:16]=[N:17][C:18]=2[CH:19]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)C>[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]2[C:14]3[N:22]([CH2:23][C:24]([NH2:27])([CH3:25])[CH3:26])[C:21]([CH2:35][O:36][CH2:37][CH3:38])=[N:20][C:15]=3[CH:16]=[N:17][C:18]=2[CH:19]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86626174tert-butyl [2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]carbamate

Product 1

HCID 670510562-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethylamineYield 92.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

HCl in ethanol (3M, 75 mL) was added to tert-butyl [2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]carbamate (5.07 g, 10.04 mmol) and the solution was heated at reflux for 15 minutes. The volatiles were removed under reduced pressure and the orange residue was partitioned between dilute aqueous hydrochloric acid and dichloromethane. The aqueous layer was washed with 2 portions of dichloromethane and then made basic with the addition of aqueous ammonium hydroxide. The aqueous fraction was then extracted with three portions of dichloromethane. The combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated to yield 3.77 g of 2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethylamine as a brown oil.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 15 minutes
  3. customThe volatiles were removed under reduced pressure
  4. customthe orange residue was partitioned between dilute aqueous hydrochloric acid and dichloromethane
  5. washThe aqueous layer was washed with 2 portions of dichloromethane
  6. additionmade basic with the addition of aqueous ammonium hydroxide
  7. extractionThe aqueous fraction was then extracted with three portions of dichloromethane
  8. washThe combined organic fractions were washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-cf0bd27484e04b81a81c0ba7d58ff461
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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