Triphenylphosphine → 2-methyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinoline-4-amine

HRID 432705Notes

Reaction equation

HRID 432705 reaction equation
[CH3:1][C:2]1[N:3]([CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]3N=N[N:16]=[C:6]3[C:5]=2[N:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+].O>ClC1C=CC=CC=1Cl.ClCCl.CCOCC>[CH3:1][C:2]1[N:3]([CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH2:16])[C:5]=2[N:17]=1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 187601655-methyl-6-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinolineHCID 23719242Sodium hydroxide--water (1/1/1)

Product 1

HCID 97990342-methyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinoline-4-amineYield 23.4%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 72391,2-DichlorobenzeneSolvent

Procedure

Under an atmosphere of nitrogen, 5-methyl-6-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline (0.73 g, 1.89 mmol) and triphenylphosphine (0.64 g, 2.84 mmol) were dissolved in 1,2-dichlorobenzene (15 ml). The reaction was heated at reflux for 18 hours. After cooling to ambient temperature, the solvent was removed in vacuo. The resulting residue was treated with 1N HCl/water (30 ml) and vigorous stirring produced an off white suspension. The solid was removed by filtration leaving a yellow filtrate. The filtrate was treated with 10% sodium hydroxide/water until pH 11 was reached. The filtrate was extracted with dichloromethane (3×25 ml). The combined organic fractions were washed with brine (25 ml), dried (Na2SO4), filtered and concentrated in vaeuo to yield an orange oil. The oil was dissolved in a minimum amount of dichloromethane and diluted with ether to produce a precipitate. The solid was recrystallized from n-propyl acetate to yield 0.16 g of 2-methyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinoline-4-amine as a tan solid, m.p. 145.0-146.0.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 hours
  3. customthe solvent was removed in vacuo
  4. additionThe resulting residue was treated with 1N HCl/water (30 ml)
  5. customproduced an off white suspension
  6. customThe solid was removed by filtration
  7. customleaving a yellow filtrate
  8. extractionThe filtrate was extracted with dichloromethane (3×25 ml)
  9. washThe combined organic fractions were washed with brine (25 ml)
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vaeuo
  13. customto yield an orange oil
  14. customto produce a precipitate
  15. customThe solid was recrystallized from n-propyl acetate

Sources & evidence

ORD record
ord-4ff2774b26e248109b42a10e3a53d1f0
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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