Ether hydrochloride → 1-{2-[(3-phenyl-2-propynyl)oxy]ethyl}1H-imidazo[4,5-c]quinolin-4-amine hydrochloride

HRID 1839090Notes

Reaction equation

HRID 1839090 reaction equation
[C:1]1([C:7]#[C:8][CH2:9][O:10][CH2:11][CH2:12][N:13]2[C:25]3[C:24]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[N:18]=[C:17]([NH2:26])[C:16]=3[N:15]=[CH:14]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:27].C(OCC)C>CO.ClCCl>[ClH:27].[C:1]1([C:7]#[C:8][CH2:9][O:10][CH2:11][CH2:12][N:13]2[C:25]3[C:24]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[N:18]=[C:17]([NH2:26])[C:16]=3[N:15]=[CH:14]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 10953452Ether hydrochlorideHCID 121142111-{2-[(3-phenyl-2-propynyl)oxy]ethyl}-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 222544211-{2-[(3-phenyl-2-propynyl)oxy]ethyl}1H-imidazo[4,5-c]quinolin-4-amine hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-{2-[(3-Phenyl-2-propynyl)oxy]ethyl}-1H-imidazo[4,5-c]quinolin-4-amine (1.0 g, 2.92 mmol) was dissolved in a mixture of methanol (15 mL) and dichloromethane (5 mL). Hydrogen chloride/diethyl ether (10 mL of 1M) was added and the reaction solution was allowed to stir for 16 hours by which time a precipitate had formed. The mixture was concentrated under reduced pressure to provide a solid. This material was recrystallized from acetonitrile containing a small amount of methanol to provide 0.52 g of 1-{2-[(3-phenyl-2-propynyl)oxy]ethyl}-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride as an off-white crystalline solid, m.p. 231-236° C.

Workup

  1. customhad formed
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto provide a solid
  4. customThis material was recrystallized from acetonitrile containing a small amount of methanol

Sources & evidence

ORD record
ord-7aa66623b7784d5cbdec12a46290a0f7
Source dataset
uspto-grants-2004_01
Patent number
US06677348B2

Reaction notes

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