Triphenylphosphine → 4-Amino-alpha,alpha-dimethyl-1H-imidazo(4,5-c)quinolin-1-ethanol

HRID 1862028Notes

Reaction equation

HRID 1862028 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][C:21]([CH3:40])([OH:39])[CH2:22][N:23]1[C:35]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]3N=N[N:38]=[C:27]3[C:26]=2[N:25]=[CH:24]1>ClC1C=CC=CC=1Cl>[NH2:38][C:27]1[C:26]2[N:25]=[CH:24][N:23]([CH2:22][C:21]([CH3:40])([CH3:20])[OH:39])[C:35]=2[C:34]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[N:28]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 11832874alpha,alpha-dimethyl-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline-6-ethanol

Product 1

HCID 1307144-Amino-alpha,alpha-dimethyl-1H-imidazo(4,5-c)quinolin-1-ethanolYield 45.9%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

Triphenylphosphine (4.5 g, 17.0 mmole) was added to a mixture of α,α-dimethyl-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline-6-ethanol (2.4 g, 8.5 mmole,Example 9) and 1,2-dichlorobenzene. The reaction mixture was heated at reflux for 3 hrs then concentrated under vacuum. The residue was combined with methanol (400 mL) and hydrochloric acid (50 mL of 0.5N) then heated on a steam bath for 2 hours. The resulting precipitate was isolated by filtration then washed with ether. The solid was dissolved in water and the solution was made basic with 10% sodium hydroxide. After stirring for 30 minutes, the reaction mixture was filtered. The collected solid was rinsed with water and ether then recrystallized from N,N-dimethylformamide/ethanol to provide about 1 g of 4-amino-α,α-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol as a solid, m.p. 271-273° C. Analysis: Calculated for C14H16N4O: %C, 65.6; %H, 6.29; %N, 21.86; Found: %C, 65.37; %H, 6.26; %N, 21.61.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hrs
  3. concentrationthen concentrated under vacuum
  4. temperaturethen heated on a steam bath for 2 hours
  5. customThe resulting precipitate was isolated by filtration
  6. washthen washed with ether
  7. dissolutionThe solid was dissolved in water
  8. filtrationthe reaction mixture was filtered
  9. washThe collected solid was rinsed with water and ether
  10. customthen recrystallized from N,N-dimethylformamide/ethanol

Sources & evidence

ORD record
ord-eb7855d64c1e4989a1e8e3e13795a28d
Source dataset
uspto-grants-2003_03
Patent number
US06534654B2

Reaction notes

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