Ammonia → HCID 9857434, compound

HRID 2119862Notes

Reaction equation

HRID 2119862 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([C:19]([CH3:22])([CH3:21])[OH:20])[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.[NH3:23]>>[NH2:23][C:2]1[C:11]2[N:12]=[C:13]([C:19]([CH3:22])([CH3:21])[OH:20])[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 15224413HCID 15224413, compound

Product 1

HCID 9857434HCID 9857434, compound

Procedure

4-Chloro-α,α-dimethyl-1-(2-methylpropyl)-1H-imidazo-[4,5-c]quinoline-2-methanol (Example 22) was aminated in a Parr bomb at 150° C. using 15% methanolic ammonia. The product was purified by silica gel column chromatography (5% methanol in ethyl acetate as eluent). The product was then recrystallized from ethyl acetate/hexane to give a solid, m.p. 214-217° C. Analysis: Calculated: C, 68.4; H, 7.4; N, 18.8. Found: C, 68.2; H, 7.4; N, 18.7.

Workup

  1. customwas aminated in a Parr bomb at 150° C.
  2. customThe product was purified by silica gel column chromatography (5% methanol in ethyl acetate as eluent)
  3. customThe product was then recrystallized from ethyl acetate/hexane
  4. customto give a solid, m.p. 214-217° C

Sources & evidence

ORD record
ord-217b45f4b59f41678546de779bb527f4
Source dataset
uspto-grants-2004_02
Patent number
US06686472B2

Reaction notes

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