Water → 3-(Hydroxymethyl)-1,2-dihydroquinolin-2-one

HRID 2225325Notes

Reaction equation

HRID 2225325 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[C:12](=[O:21])[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)=O.O.S(=O)(=O)(O)O>O1CCCC1>[OH:8][CH2:9][C:11]1[C:12](=[O:21])[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 277384Methyl 2-oxo-1,2-dihydroquinoline-3-carboxylateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 27645783-(Hydroxymethyl)-1,2-dihydroquinolin-2-oneYield 26.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

16 Grams of lithium aluminum hydride was suspended in 200 ml of dried tetrahydrofuran, then 16 g of 3-methoxycarbonylcarbostyril was added thereto at a room temperature with stirring. The reaction mixture was further stirred for 5 hours at a room temperature. The excess lithium aluminum hydride in the reaction mixture was decomposed by adding ethyl acetated dropwise. Further, water was added to the reaction mixture and concentrated under a reduced pressure to obtain residue. To the residue was added a diluted sulfuric acid and the precipitated crystals were collected by filtration and recrystallized from methanol to obtain 3.7 g of 3-hydroxymethylcarbostyril in the form of colorless prism-like crystals.

Workup

  1. stirringThe reaction mixture was further stirred for 5 hours at a room temperature
  2. additionby adding ethyl
  3. concentrationconcentrated under a reduced pressure
  4. customto obtain residue
  5. filtrationthe precipitated crystals were collected by filtration
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-c5a4c558f7a145a09da3e5200daf6f91
Source dataset
uspto-grants-1994_09
Patent number
USRE034722

Reaction notes

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