Methanol → HCID 15231843, compound

HRID 1757102Notes

Reaction equation

HRID 1757102 reaction equation
C1(C[N:8](CC2C=CC=CC=2)[C:9]2[C:18]3[N:19]=[C:20]([CH3:26])[N:21]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:17]=3[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[N:10]=2)C=CC=CC=1.C([O-])=O.[NH4+].CO.[OH-].[NH4+]>Cl.[OH-].[OH-].[Pd+2]>[CH3:26][C:20]1[N:21]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:17]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[N:10]=[C:9]([NH2:8])[C:18]=2[N:19]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 2723923Ammonium formate2×HCID 67758872HCID 67758872, compound

Product 1

HCID 15231843HCID 15231843, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 313Hydrochloric AcidSolvent

Procedure

N,N-Bis(phenylmethyl)-6,7,8,9-tetrahydro-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (820 mg, 1.87 mmole), palladium hydroxide on carbon (200 mg, Pearlman's catalyst), ammonium formate (472 mg, 7.48 mmole) and methanol (50 mL) were combined and heated at reflux for 48 hours. During the course of the reaction additional catalyst (200 mg) and ammonium formate (472 mg) were added. The reaction mixture was cooled to ambient temperature then filtered through a layer of celite. The filtrate was evaporated to provide a residue which was dissolved in 3N hydrochloric acid. The solution was made basic (pH 9) with ammonium hydroxide then extracted with methylene chloride (3×200 mL). The extracts were combined, washed with water, dried over magnesium sulfate then concentrated to provide 480 mg of a white solid. This solid was recrystallized from ethyl acetate to provide 260 mg of the desired product as a white solid, m.p. 170°-172° C. Analysis: Calculated for C5H22N4 +1/3H2O: % C, 68.16; % H, 8.64; % N, 21.2; Found: % C, 68.47; % H, 8.14; % N, 21.08.

Workup

  1. temperatureheated
  2. temperatureat reflux for 48 hours
  3. filtrationthen filtered through a layer of celite
  4. customThe filtrate was evaporated
  5. customto provide a residue which
  6. extractionthen extracted with methylene chloride (3×200 mL)
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationthen concentrated

Sources & evidence

ORD record
ord-5ddc1a4431394590b4bcc8c327cc3838
Source dataset
uspto-grants-1995_08
Patent number
US05444065

Reaction notes

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