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Acetic Acid → 4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-C]quinoline-2-methanol

HRID 396950
Notes
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Reaction equation

HRID 396950 reaction equation
[Cl:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.CC1C([C:26](O)=[O:27])=CC=CC=1.C[O-].[Na+].C(OCC)(=O)C.C(O)(=O)C>CO>[Cl:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:26][OH:27])[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 88033762HCID 88033762, compound

Product 1

HCID 152244014-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-C]quinoline-2-methanolYield 71.4%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

4-Chloro-1-(2-methylpropyl)-1H-imidazo-[4,5-c]quinoline-2-methyl benzoate (14.3 g; 0.36 mol, Example 7) was suspended in dry methanol (350 mL). The mixture was made basic (pH 10) with 25% sodium methoxide. The mixture was stirred at room temperature for 5 hr after which time only a trace of starting material was detected by silica gel TLC (ethyl acetate eluent). The mixture was made acidic with acetic acid and then concentrated to dryness. The residue was slurried in ether. The solid was filtered from the mixture and then suspended in aqueous sodium hydroxide. The product was filtered from the mixture, washed with water, and dried to yield 7.5 g (71.4%) of tan solid. The product was recrystallized from ethanol to yield 4.8 g of pure product m.p. 162-166° C. Analysis: Calculated: C, 62.2; H, 5.6; N, 14.5. Found: C, 62.2; H, 5.6; N, 14.3.

Workup

  1. concentrationconcentrated to dryness
  2. filtrationThe solid was filtered from the mixture
  3. filtrationThe product was filtered from the mixture
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-e4a3f907b1fd47cb8641f43014b4f872
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06608201B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes