Hydrochloric Acid → HCID 178448406, compound

HRID 374977Notes

Reaction equation

HRID 374977 reaction equation
Cl.[C:2]1([CH2:8][N:9]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:10]2[C:19]3[N:20]=[C:21]([CH2:27][CH2:28][CH:29]([CH3:32])[CH2:30][Cl:31])[N:22](COCC)[C:18]=3[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C(Cl)Cl>[C:34]1([CH2:33][N:9]([CH2:8][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]2[C:19]3[N:20]=[C:21]([CH2:27][CH2:28][CH:29]([CH3:32])[CH2:30][Cl:31])[NH:22][C:18]=3[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18995660HCID 18995660, compound

Product 1

HCID 178448406HCID 178448406, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Hydrochloric acid (80 mL of 6N) was added to a suspension of N,N-bis(phenylmethyl)-2-(4-chloro-3-methylbutyl)-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (0.64 g, 1.2 mmole) in methanol (40 mL). The reaction mixture was heated at reflux for 2 hours (All of the methanol was driven off during this period.), diluted with methylene chloride and then made basic with 10% sodium hydroxide. The methylene chloride layer was separated, dried over magnesium sulfate and then concentrated to provide about 0.5 g of N,N-bis(phenylmethyl)-2-(4-chloro-3-methylbutyl)-1H-imidazo[4,5-c]quinolin-4-amine.

Workup

  1. temperatureThe reaction mixture was heated
  2. waitwas driven off during this period
  3. customThe methylene chloride layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c1f245b5bec34fa0a4d2822f82954db2
Source dataset
uspto-grants-1996_01
Patent number
US05482936

Reaction notes

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