HCID 13982918, compound → HCID 13958392, compound

HRID 255522Notes

Reaction equation

HRID 255522 reaction equation
C([O:4][CH:5]([CH2:21][O:22]C(=O)C)[CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N+:12]([O-:20])=[CH:11][C:10]=2[N:9]=[CH:8]1)(=O)C>CO.C[O-].[Na+]>[OH:4][CH:5]([CH2:21][OH:22])[CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N+:12]([O-:20])=[CH:11][C:10]=2[N:9]=[CH:8]1

Participants

4

Reactant 1

HCID 13982918HCID 13982918, compound

Product 1

HCID 13958392HCID 13958392, compound

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 4.0 g (0.0117 mole) of 1-(2,3-diacetoxypropyl)-1H-imidazo[4,5-c]quinolin-5-oxide (from Example 124, Part B) in 50 ml of methanol was added about 12 drops of 25% sodium methoxide solution. After one hour the product was collected by filtration, washed with methanol and recrystallized from ethanol to provide 1-(2,3-dihydroxypropyl)-1H-imidazo[4,5-c]quinolin-5-oxide, m.p. 240°-242° C. Analysis: Calculated for C13H13N3O3 : %C, 60.2; %H, 5.1; %N, 16.2; Found: %C, 60.0; %H, 5.0; %N, 15.8.

Workup

  1. filtrationAfter one hour the product was collected by filtration
  2. washwashed with methanol
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-343d78e1aa71417a80529ee2a2163fc5
Source dataset
uspto-grants-1987_10
Patent number
US04698348

Reaction notes

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