Methoxyacetic Acid → alpha,alpha-Dimethyl-2-methoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

HRID 274396

Reaction equation

HRID 274396 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([OH:17])([CH3:16])[CH3:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:18][O:19][CH2:20][C:21](O)=O>C(OCC)(=O)C>[CH3:16][C:14]([CH3:15])([OH:17])[CH2:13][N:12]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[C:21]1[CH2:20][O:19][CH3:18]

Participants

4

Reactant 2

HCID 12251Methoxyacetic AcidHCID 149869411-((3-Aminoquinolin-4-yl)amino)-2-methylpropan-2-ol

Product 1

HCID 15224447alpha,alpha-Dimethyl-2-methoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanolYield 9.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
170 °C

Procedure

3-Amino-4-(2-hydroxy-2-methylpropylamino)quinoline (7.5 g, 32 mmol) was combined with methoxyacetic acid (7.5 mL, 97 mmol) and heated at about 170° C. for about 3 hours. The resulting solid residue was dissolved in ethyl acetate (150 mL). The ethyl acetate solution was extracted twice with 0.2N sodium hydroxide, washed with water, dried over magnesium sulfate, treated with activated charcoal and then concentrated to a volume of about 50 mL. Hexane was added to the ethyl acetate and the resulting precipitate was collected and dried to provide 0.9 g of the desired product as a crystalline solid, m.p. 145°-148° C.

Workup

  1. extractionThe ethyl acetate solution was extracted twice with 0.2N sodium hydroxide
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. additiontreated with activated charcoal
  5. concentrationconcentrated to a volume of about 50 mL
  6. additionHexane was added to the ethyl acetate
  7. customthe resulting precipitate was collected
  8. customdried

Sources & evidence

ORD record
ord-3d10098f09b04188a27c419d4b6f03fd
Source dataset
uspto-grants-1995_02
Patent number
US05389640

Linked notes

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