Methanol → HCID 178478462, compound

HRID 374973Notes

Reaction equation

HRID 374973 reaction equation
CO.[C:3]1([CH2:9][N:10]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:11]2[C:20]3[N:21]=[C:22]([CH2:28][CH2:29][CH2:30][CH2:31][Cl:32])[N:23](COCC)[C:19]=3[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>Cl>[C:3]1([CH2:9][N:10]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:11]2[C:20]3[N:21]=[C:22]([CH2:28][CH2:29][CH2:30][CH2:31][Cl:32])[NH:23][C:19]=3[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 18995646HCID 18995646, compound

Product 1

HCID 178478462HCID 178478462, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Methanol (several mL) was added to a suspension of N,N-bis(phenylmethyl)-2-(4-chlorobutyl)-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (0.76 g, 1.5 mmole) in 3N hydrochloric acid (20 mL). The reaction mixture was heated on a stream bath for 4 hours then partitioned between methylene chloride and aqueous saturated sodium bicarbonate. The methylene chloride layer was separated, dried over magnesium sulfate and then concentrated under vacuum to provide 0.64 g of N,N-bis(phenylmethyl)-2-(4-chlorobutyl)-1H-imidazo[4,5-c]quinolin-4-amine.

Workup

  1. temperatureThe reaction mixture was heated on a stream bath for 4 hours
  2. customthen partitioned between methylene chloride and aqueous saturated sodium bicarbonate
  3. customThe methylene chloride layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f21899cbb2254a049e44605a80bed318
Source dataset
uspto-grants-1996_01
Patent number
US05482936

Reaction notes

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