Formaldehyde → 4-bis(phenylmethyl)amino-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-2-methanol

HRID 374986

Reaction equation

HRID 374986 reaction equation
C([Li])CCC.[C:6](=[O:8])=O.CC(C)=O.[C:13]1([CH2:19][N:20]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:21]2[C:30]3[N:31]=[CH:32][N:33]([CH2:34][O:35][CH2:36][CH3:37])[C:29]=3[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:22]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)=O.C(Cl)(Cl)(Cl)Cl.C=O>O1CCCC1>[C:39]1([CH2:38][N:20]([CH2:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:21]2[C:30]3[N:31]=[C:32]([CH2:6][OH:8])[N:33]([CH2:34][O:35][CH2:36][CH3:37])[C:29]=3[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:22]=2)[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 18522661Acetone cardiceHCID 18995666N,N-bis(phenylmethyl)-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amineHCID 86602444Carbontetrachloride dry-iceHCID 178418339Butyllithium

Product 1

HCID 189956654-bis(phenylmethyl)amino-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-2-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Butyllithium (1.6 mL of 2.5M in hexanes, 4 mmole) was added to a chilled (dry ice/acetone bath) solution of N,N-bis(phenylmethyl)-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (1.7 g, 4 mmole) in tetrahydrofuran. No color change was observed. The reaction mixture was warmed to -20° C. (dry ice/carbon tetrachloride) and the reaction turned red in color. Formaldehyde gas entrained in a flow of nitrogen was added to the reaction mixture. After several minutes the reaction turned to a solid mass and the ice bath was removed. The reaction mixture was allowed to warm to ambient temperature and the color of the reaction mixture changed from red to yellow. The reaction was diluted with diethyl ether and water. The ether layer was separated, dried over magnesium sulfate and then concentrated under vacuum. The residue was purified by column chromatography (silica gel eluting with 10-20% ethyl acetate in hexanes v/v) to provide 1 g of 4-bis(phenylmethyl)amino-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-2-methanol.

Workup

  1. additionwas added to the reaction mixture
  2. waitAfter several minutes the reaction turned to a solid mass
  3. customthe ice bath was removed
  4. additionThe reaction was diluted with diethyl ether and water
  5. customThe ether layer was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by column chromatography (silica gel eluting with 10-20% ethyl acetate in hexanes v/v)

Sources & evidence

ORD record
ord-db242ccd6c31490594b3cf4e65d94c64
Source dataset
uspto-grants-1996_01
Patent number
US05482936

Linked notes

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