Acetic Acid → HCID 18957126, compound

HRID 2379430Notes

Reaction equation

HRID 2379430 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][C:8]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27])=[CH:17][CH:16]=[CH:15][C:14]=2[O:28][CH3:29])=[O:9])=[O:5])[CH3:2].[BH4-].[Na+].C(O)(=O)C>CO>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH:8]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27])=[CH:17][CH:16]=[CH:15][C:14]=2[O:28][CH3:29])[OH:9])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1924943-(3-(Ethoxycarbonyl)propionyl)-8-methoxy-4-((2-methylphenyl)amino)quinoline2×HCID 4311764Sodium borohydride2×

Product 1

HCID 18957126HCID 18957126, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

A well-stirred suspension consisting of 3.59 g (0.00915 mole) of 3-(3-ethoxycarbonylpropionyl)-8-methoxy-4-(2-methylphenylamino)-quinoline (the product of Example 1) in 200 mL of methanol was cooled to 5° C. and 173 mg. (0.0045 mole) of sodium borohydride (available from the Aldrich Chemical Company, Inc. of Milwaukee, Wis.) was immediately thereafter slowly added in small-divided portions, followed by continued stirring of the reaction mixture at 5° C. for a period of 45 minutes. At this point, a fresh batch of 90 mg of sodium borohydride was added to the stirred reaction mixture and further stirring was then continued at 5° C. for a period of one hour. Upon completion of this step, the pH of the resulting homogeneous solution was next adjusted to a value of pH 7 by the careful addition of glacial acetic acid, followed by filtration and subsequent evaporation of the resulting filtrate under reduced pressure to eventually give a crystalline product as the residue. Recrystallization of the latter material from methanol-water then gave a nearly quantitative yield of pure 3-(3-ethoxycarbonyl-1-hydroxypropyl)-8-methoxy-4-(2-methyl-phenylamino)quinoline as a partial hemihydrate, m.p. 133°-135° C. The pure product was further characterized by means of mass spectrum (MS) analysis and nuclear magnetic resonance (NMR) data, in addition to elemental analysis.

Workup

  1. addition) was immediately thereafter slowly added in small-divided portions
  2. stirringfurther stirring
  3. waitwas then continued at 5° C. for a period of one hour
  4. filtrationfollowed by filtration and subsequent evaporation of the resulting filtrate under reduced pressure
  5. customto eventually give a crystalline product as the residue
  6. customRecrystallization of the latter material from methanol-water

Sources & evidence

ORD record
ord-5c36c139b6c54f4c85bbf5cb305b328d
Source dataset
uspto-grants-1994_11
Patent number
US05362743

Reaction notes

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