Dichloromethane → HCID 69878358, compound

HRID 1601683Notes

Reaction equation

HRID 1601683 reaction equation
C([O:4][CH:5]([C:10]1[N:11]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:12]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[C:14]([NH2:22])[C:13]=2[N:23]=1)[CH2:6][CH2:7][CH2:8][CH3:9])(=[O:3])C.C(Cl)Cl>C[O-].[Na+].CO>[OH2:3].[NH2:22][C:14]1[C:13]2[N:23]=[C:10]([CH:5]([CH2:6][CH2:7][CH2:8][CH3:9])[OH:4])[N:11]([CH2:24][CH:25]([CH3:26])[CH3:27])[C:12]=2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1.[NH2:22][C:14]1[C:13]2[N:23]=[C:10]([CH:5]([CH2:6][CH2:7][CH2:8][CH3:9])[OH:4])[N:11]([CH2:24][CH:25]([CH3:26])[CH3:27])[C:12]=2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 15224431HCID 15224431, compound

Product 1

HCID 69878358HCID 69878358, compoundYield 24.2%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 887MethanolSolvent2×

Procedure

Several drops of 25% sodium methoxide in methanol were added to a solution of 2-(1-acetoxypentyl)-1-(2-methylpropyl)-1H-imidazo-[4,5-c]quinolin-4-amine (12 g; 32 mmol, Example 59) in methanol and the resulting mixture was heated at reflux for about one hour. The reaction was concentrated under vacuum to provide a solid. A portion of this solid was taken up in a large volume of methylene chloride, washed with water, dried over magnesium sulfate and reduced to a volume of about 50 mL. The resulting precipitate was collected and dried to provide 2.6 g of a white crystalline solid, m.p. 208-211° C. Analysis: Calculated: C, 68.0; H, 8.1; N, 16.7; Found: C, 67.8; H, 7.7; N, 16.6.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for about one hour
  3. concentrationThe reaction was concentrated under vacuum
  4. customto provide a solid
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customThe resulting precipitate was collected
  8. customdried

Sources & evidence

ORD record
ord-3fc6205efc90482781d5cd1d5eac6574
Source dataset
uspto-grants-1999_11
Patent number
US05977366

Reaction notes

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