8-benzyloxy-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine → 4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-ol

HRID 2203623Notes

Reaction equation

HRID 2203623 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[C:14]([NH2:19])[C:13]3[N:20]=[C:21]([CH2:26][O:27][CH2:28][CH3:29])[N:22]([CH2:23][CH2:24][CH3:25])[C:12]=3[C:11]=2[CH:10]=1)C1C=CC=CC=1>[Pd].C(O)C.CO>[NH2:19][C:14]1[C:13]2[N:20]=[C:21]([CH2:26][O:27][CH2:28][CH3:29])[N:22]([CH2:23][CH2:24][CH3:25])[C:12]=2[C:11]2[CH:10]=[C:9]([OH:8])[CH:18]=[CH:17][C:16]=2[N:15]=1

Participants

4

Reactant 1

HCID 575453188-benzyloxy-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 689719384-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-olYield 61.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

A dispersion of 8-benzyloxy-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine (22.0 g, 56.3 mmol) and 10% palladium on carbon (7.5 g) in 50:50 ethanol/methanol (300 mL) was shaken under hydrogen pressure on a Parr apparatus at 50 psi (3.4×105 Pa) for three days. The reaction mixture was filtered to remove the catalyst, which was washed with hot ethanol/methanol (3 L). The filtrate was concentrated under reduced pressure. The resulting solid was triturated with methanol and isolated by filtration to provide 10.4 g of 4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-ol as an off-white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst, which
  3. washwas washed with hot ethanol/methanol (3 L)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe resulting solid was triturated with methanol
  6. customisolated by filtration

Sources & evidence

ORD record
ord-9ca66770965e4634aede7ab80a57d7f0
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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