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

HRID 1006592
Notes
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Reaction equation

HRID 1006592 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-2d6e1a1dafcb40919091388cab654f9a
Source dataset
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06790961B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes