Ammonia → HCID 9856687, compound

HRID 396951Notes

Reaction equation

HRID 396951 reaction equation
Cl[C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][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.CC1C([C:26]([OH:28])=O)=CC=CC=1.[NH3:29]>>[NH2:29][C:2]1[C:11]2[N:12]=[C:13]([CH2:26][OH:28])[N:14]([CH2:15][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

Participants

3

Reactant 2

HCID 222AmmoniaHCID 88033762HCID 88033762, compound

Product 1

HCID 9856687HCID 9856687, compound

Conditions

Temperature
175 °C

Procedure

4-Chloro-1-(2-methylpropyl)-1H-imidazo-[4,5-c]quinoline-2-methyl benzoate (5.0 g; 0.13 mol, Example 7) was added to 15% methanolic ammonia (50 mL). The mixture was heated in a Parr bomb for 7 hr at 175° C. The resulting solution was evaporated to reduce the volume. A sticky solid crystallized from the solution. The solid was filtered from the mixture and slurried in aqueous sodium bicarbonate solution. The resulting solid was filtered from the mixture, washed with water, and dried to yield 2.1 g (61.7%) of crude product which was recrystallized from ethanol several times to yield pure product m.p. 226-231° C. Analysis: Calculated: C, 66.6: H, 6.7; N, 20.7. Found: C, 66.4; H, 6.5; N, 20.4.

Workup

  1. customThe resulting solution was evaporated
  2. customA sticky solid crystallized from the solution
  3. filtrationThe solid was filtered from the mixture
  4. filtrationThe resulting solid was filtered from the mixture
  5. washwashed with water
  6. customdried
  7. customto yield 2.1 g (61.7%) of crude product which
  8. customwas recrystallized from ethanol several times

Sources & evidence

ORD record
ord-599c52768b734fd3bdab3becfaef378c
Source dataset
uspto-grants-2003_08
Patent number
US06608201B2

Reaction notes

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