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

HRID 1168568Notes

Reaction equation

HRID 1168568 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 hous. 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 form 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 C14H16NO: %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 hous
  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
  11. customform N,N-dimethylformamide/ethanol

Sources & evidence

ORD record
ord-30c7e52872e447a0923b5548d5e5b781
Source dataset
uspto-grants-2003_09
Patent number
US06624305B2

Reaction notes

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