Ammonia → HCID 9857046, compound

HRID 396957Notes

Reaction equation

HRID 396957 reaction equation
Cl[C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH:15](C)[CH:16]([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.CC1[C:26]([C:27]([OH:29])=O)=CC=CC=1.[NH3:30]>>[NH2:30][C:2]1[C:11]2[N:12]=[C:13]([CH:27]([CH3:26])[OH:29])[N:14]([CH2:15][CH:16]([CH3:17])[CH3:18])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 131718852HCID 131718852, compound

Product 1

HCID 9857046HCID 9857046, compound

Conditions

Temperature
165 °C

Procedure

4-Chloro-α-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-methyl benzoate (3.7 g; 0.009 mol, Example 19) was added to 15% methanolic ammonia (50 mL). The mixture was heated in a Parr bomb at 165° C. for 6 hr. The resulting reaction mixture was evaporated and the residue was slurried in aqueous sodium bicarbonate. The product was extracted into dichloromethane, and the extracts were washed with aqueous sodium bicarbonate and dried over magnesium sulfate. The organic extracts were evaporated to dryness to yield an oily solid. The solid was purified by silica gel column chromatography to yield two products, the intended product and the 4-(N-methyl) derivative. The intended product Rf=0.36 silica gel TLC, ethyl acetate eluent) was recrystallized from ethanol to yield a solid m.p. 190-195° C. Analysis: Calculated: C, 67.6; H, 7.1; N, 19.7. Found: C, 67.6; H, 7.1; N, 19.7. The 4-(N-methyl) derivative was recrystallized from ethyl acetate to give a solid, m.p. 145-149° C. Analysis: Calculated: C, 68.4; H, 7.4; N, 18.8. Found: C, 68.3; H, 7.4; N, 18.7.

Workup

  1. customThe resulting reaction mixture
  2. customwas evaporated
  3. extractionThe product was extracted into dichloromethane
  4. washthe extracts were washed with aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. customThe organic extracts were evaporated to dryness
  7. customto yield an oily solid
  8. customThe solid was purified by silica gel column chromatography
  9. customto yield two products
  10. customThe intended product Rf=0.36 silica gel TLC, ethyl acetate eluent) was recrystallized from ethanol

Sources & evidence

ORD record
ord-b744b713fe6444ddad3f851e06c90db5
Source dataset
uspto-grants-2003_08
Patent number
US06608201B2

Reaction notes

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