Chloroform → 8-benzyloxy-2-ethyl-1-methyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 598307Notes

Reaction equation

HRID 598307 reaction equation
C(Cl)(Cl)Cl.[CH2:5]([O:12][C:13]1[CH:22]=[CH:21][C:20]2[N+:19]([O-])=[CH:18][C:17]3[N:24]=[C:25]([CH2:28][CH3:29])[N:26]([CH3:27])[C:16]=3[C:15]=2[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.ClC(Cl)(Cl)C([N:34]=C=O)=O.C[O-].[Na+]>ClCCl.CO>[CH2:5]([O:12][C:13]1[CH:22]=[CH:21][C:20]2[N:19]=[C:18]([NH2:34])[C:17]3[N:24]=[C:25]([CH2:28][CH3:29])[N:26]([CH3:27])[C:16]=3[C:15]=2[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 6212Chloroform2×HCID 76400Trichloroacetyl isocyanateHCID 10942334Sodium MethoxideHCID 670509858-benzyloxy-2-ethyl-1-methyl-5-oxido-1H-imidazo[4,5-c]quinoline

Product 1

HCID 575453468-benzyloxy-2-ethyl-1-methyl-1H-imidazo[4,5-c]quinolin-4-amineYield 73.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A modification of the general method of Part C of Example 3 was used. Chloroform (10 mL) was added to the solution of 8-benzyloxy-2-ethyl-1-methyl-5-oxido-1H-imidazo[4,5-c]quinoline (1.30 g, 3.90 mmol) in dichloromethane (35 mL) to improve the solubility. After the addition of trichloroacetyl isocyanate (0.633 mL, 5.31 mmol), the reaction was stirred for 3.5 hours. In the second step, chloroform (10 mL) was also added to the suspension in methanol (30 mL). After the reaction with sodium methoxide, the reaction was stirred over two nights, and the precipitate was isolated by filtration, washed with hexanes, recrystallized from methanol (278 mL/g), isolated by filtration, washed with hexanes, and dried for two days in a vacuum oven. A second crop of crystals from the mother liquor was combined with the first to provide 0.95 g of 8-benzyloxy-2-ethyl-1-methyl-1H-imidazo[4,5-c]quinolin-4-amine as a white crystalline solid, mp 238.4-238.9° C.

Workup

  1. stirringthe reaction was stirred over two nights
  2. customthe precipitate was isolated by filtration
  3. washwashed with hexanes
  4. customrecrystallized from methanol (278 mL/g)
  5. customisolated by filtration
  6. washwashed with hexanes
  7. customdried for two days in a vacuum oven

Sources & evidence

ORD record
ord-d412bd39ee6c4b44bab551fb3aba5d92
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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