Sodium Hydroxide → HCID 178478464, compound

HRID 374980Notes

Reaction equation

HRID 374980 reaction equation
[C:1]1([CH2:7][N:8]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:9]2[C:18]3[N:19]=[C:20]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][Cl:31])[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(Cl)Cl>[C:33]1([CH2:32][N:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:9]2[C:18]3[N:19]=[C:20]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][Cl:31])[NH:21][C:17]=3[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18995649HCID 18995649, compound

Product 1

HCID 178478464HCID 178478464, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of N,N-bis(phenylmethyl)-2-(5-chloropentyl)-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (1.5 g, 3 mmole) in 6N hydrochloric acid (100 mL) was heated at reflux for 1 hour. The reaction mixture was cooled, diluted with methylene chloride, made basic with 10% sodium hydroxide and then extracted with methylene chloride (400 mL total). The methylene chloride extracts were combined, dried over magnesium sulfate and then concentrated under vacuum to provide about 1.3 g of N,N-bis(phenylmethyl)-2-(5-chloropentyl)-1H-imidazo[4,5-c]quinolin-4-amine.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with methylene chloride (400 mL total)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4cd07b9d9bc04f178898c04f19bfd028
Source dataset
uspto-grants-1996_01
Patent number
US05482936

Reaction notes

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