Sodium Hydroxide → 1-[2-(2-aminoethoxy)ethyl]-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine

HRID 1826164Notes

Reaction equation

HRID 1826164 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[C:8]1[CH2:21][CH2:22][O:23][CH3:24].[OH-].[Na+]>FC(F)(F)C(O)=O.O.O=[Pt]=O>[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[C:8]1[CH2:21][CH2:22][O:23][CH3:24]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 121062041-[2-(2-Aminoethoxy)ethyl]-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 120960451-[2-(2-aminoethoxy)ethyl]-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amineYield 56.8%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalyst2×HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

1-[2-(2-Aminoethoxy)ethyl]-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine (10.0 g, 27.3 mmol) was dissolved in 50 mL of trifluoroacetic acid and treated with PtO2 (1.0 g). The reaction mixture was shaken under H2 (3 Kg/cm2). After 4 d, an additional 0.5 g of PtO2 was added and hydrogenation was continued for an additional 3 d. The reaction was then filtered through Celite and concentrated under reduced pressure to give a brown oil. The oil was dissolved in 200 mL of H2O then made basic (pH˜11) by addition of 10% NaOH solution. This was then extracted with CHCl3 (5×75 mL) and the combined organic layers were dried over Na2SO4 and concentrated to give 5.17 g of 1-[2-(2-aminoethoxy)ethyl]-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine as a tan solid.

Workup

  1. waithydrogenation was continued for an additional 3 d
  2. filtrationThe reaction was then filtered through Celite
  3. concentrationconcentrated under reduced pressure
  4. customto give a brown oil
  5. extractionThis was then extracted with CHCl3 (5×75 mL)
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f9c0f170942e45e78e51dbeb09582ef1
Source dataset
uspto-grants-2006_05
Patent number
US07049439B2

Reaction notes

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