Sodium Hydroxide → HCID 178478459, compound

HRID 374983Notes

Reaction equation

HRID 374983 reaction equation
[C:1]1([CH2:7][N:8]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:9]2[C:18]3[N:19]=[C:20]([CH2:26][CH2:27][CH2:28][Cl:29])[N:21](COCC)[C:17]=3[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>Cl>[C:1]1([CH2:7][N:8]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:9]2[C:18]3[N:19]=[C:20]([CH2:26][CH2:27][CH2:28][Cl:29])[NH:21][C:17]=3[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18995653HCID 18995653, compound

Product 1

HCID 178478459HCID 178478459, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of N,N-bis(phenylmethyl)-2-(3-chloropropyl)-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (1 g, 2.0 mmole) in 6N hydrochloric acid (80 mL) was heated at reflux for 2 hours and then stirred at ambient temperature overnight. The reaction mixture was neutralized with 10% sodium hydroxide then extracted with methylene chloride. The extract was dried over magnesium sulfate then concentrated under vacuum to provide 0.8 g of N,N-bis(phenylmethyl)-2-(3-chloropropyl)-1H-imidazo[4,5-c]quinolin-4-amine.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. extractionthen extracted with methylene chloride
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationthen concentrated under vacuum

Sources & evidence

ORD record
ord-0c13626a7a944cce8d8668d11a53439e
Source dataset
uspto-grants-1996_01
Patent number
US05482936

Reaction notes

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