Water → HCID 12245445, compound

HRID 649270Notes

Reaction equation

HRID 649270 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13](OCC)=[O:14])=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24].[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([CH2:13][OH:14])=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24]

Participants

6

Reactant 4

HCID 962WaterHCID 166653HydrideHCID 12245443HCID 12245443, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12245445HCID 12245445, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3.5 g (0.01 mol) of ethyl 6-chloro-4-(2-fluorophenyl)quinolin-2(1H)-one-3-carboxylate,* in 50 ml of tetrahydrofuran was added to a suspension of 1 g (0.022 mol) of lithium aluminum hydride in 50 ml of tetrahydrofuran. After stirring for 30 min at -20° to 0°, the hydride was hydrolized by addition of 5 ml of water. The mixture was then partitioned between methylene chloride and 2N hydrochloric acid. The methylene chloride layer was washed with water dried and evaporated. Crystallization of the residue from ethanol/chloroform yielded 6-chloro-4-(2-fluorophenyl)-3-hydroxymethylquinolin-2(1H)-one, with mp 282°-286°.

Workup

  1. customThe mixture was then partitioned between methylene chloride and 2N hydrochloric acid
  2. washThe methylene chloride layer was washed with water
  3. customdried
  4. customevaporated
  5. customCrystallization of the residue from ethanol/chloroform

Sources & evidence

ORD record
ord-a25c1dd63018423e8b0e5f12d7b63d4c
Source dataset
uspto-grants-1988_04
Patent number
US04739049

Reaction notes

Loading…