Tetrahydrofuran → HCID 20340829, compound

HRID 1395281Notes

Reaction equation

HRID 1395281 reaction equation
[Cl:1][C:2]1[C:11]2[C:10](C(OCC)=O)=[C:9]([Cl:17])[CH:8]=[CH:7][C:6]=2[N:5]=[CH:4][CH:3]=1.[O:18]1CCC[CH2:19]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:17])[CH:10]=2)[N:5]=[CH:4][C:3]=1[CH2:19][OH:18]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86736980HCID 86736980, compound

Product 1

HCID 20340829HCID 20340829, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

27 g. of 4,6-dichloroquinoline-5-carboxylic acid, ethyl ester (0.1 mol.) are dissolved in 600 ml. of anhydrous tetrahydrofuran. Nitrogen is passed through the flask and while stirring and cooling to 0°, 2.4 g. of lithium aluminum hydride are added a bit at a time in order to keep the reaction temperature at 0° to +5°. Stirring is continued for an additional five hours. Then 2.5 ml. of water, 2.0 ml. of aqueous sodium hydroxide (20%) and again 9 ml. of water are added. The precipitated inorganic salts are filtered off and the solvent is removed by a rotary evaporator. The resulting oil is dissolved in a small quantity of benzene and kept in the refrigerator. The crystallized 4,6-dichloroquinoline-3-methanol is filtered off and recrystallized from ethyl acetate; yield: 12.5 g. (55%); m.p 182°.

Workup

  1. temperaturecooling to 0°
  2. customat 0° to +5°
  3. stirringStirring
  4. filtrationThe precipitated inorganic salts are filtered off
  5. customthe solvent is removed by a rotary evaporator
  6. dissolutionThe resulting oil is dissolved in a small quantity of benzene
  7. filtrationThe crystallized 4,6-dichloroquinoline-3-methanol is filtered off
  8. customrecrystallized from ethyl acetate
  9. customm.p 182°

Sources & evidence

ORD record
ord-e6d17f95de264bcbafa775935f98cbd2
Source dataset
uspto-grants-1980_05
Patent number
US04202985

Reaction notes

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