Ammonia → HCID 22254492, compound

HRID 433988Notes

Reaction equation

HRID 433988 reaction equation
Cl[C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH:16]([CH3:19])[CH2:17][OH:18])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[OH-].[K+].[NH3:22]>>[NH2:22][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH:16]([CH3:19])[CH2:17][OH:18])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 14797Potassium HydroxideHCID 22254442HCID 22254442, compound

Product 1

HCID 22254492HCID 22254492, compound

Procedure

R 3-(4-Chloro-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-1-ol (1.0 g, 3.6 mmol) and methanolic ammonia (30 mL of 15%) were combined and then heated in a steel bomb at 150° C. The container was allowed to cool to ambient temperature. Excess methanolic potassium hydroxide was added to the reaction mixture which was then concentrated under reduced pressure to decrease the volume. Water was added and then concentration was continued until a solid formed. The solid was isolated by filtration, washed with water and then dried to provide a near white solid. This material was recrystallized from methanol/dichloromethane to provide R 3-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-1-ol as colorless solid, m.p. 258-261° C. Analysis: Calculated for C14H16N4O: %C, 65.61, %H, 6.29; %N, 21.86; Found: %C, 65.50, %H, 6.3, %N, 21.7.

Workup

  1. concentrationwas then concentrated under reduced pressure
  2. additionWater was added
  3. concentrationconcentration
  4. customformed
  5. customThe solid was isolated by filtration
  6. washwashed with water
  7. customdried
  8. customto provide a near white solid
  9. customThis material was recrystallized from methanol/dichloromethane

Sources & evidence

ORD record
ord-f36b2ace5500474689e6f45b20f47f64
Source dataset
uspto-grants-2003_12
Patent number
US06670372B2

Reaction notes

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