Sodium borohydride → 6-(2-Hydroxyethoxy)-1,2,3,4-tetrahydroquinolin-2-one

HRID 1023201Notes

Reaction equation

HRID 1023201 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][C:14](OCC)=[O:15])[CH:8]=2)[NH:3]1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>C(O)C.CCOC(C)=O>[OH:15][CH2:14][CH2:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2](=[O:1])[CH2:11][CH2:10]2

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 12821879Ethyl 2-[(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy]acetate

Product 1

HCID 133921376-(2-Hydroxyethoxy)-1,2,3,4-tetrahydroquinolin-2-oneYield 72.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of ethyl 2-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)acetate (1.5 g, 6.02 mmol) in ethanol (25 mL), was added calcium chloride (0.334 g, 3.01 mmol). The resulting mixture was cooled to −10° C. and NaBH4 (0.455 g, 12.04 mmol) was added, then stirred at 23° C. for 5 h. The reaction mixture was diluted with EtOAc (50 ml), extracted with sat NaHCO3 solution and brine, dried over anhydrous sodium sulfate, and concentrated to afford a white solid. The crude material was purified by silica gel flash chromatography (12 g, 40-100% ethyl acetate in hexanes) to afford 6-(2-hydroxyethoxy)-3,4-dihydroquinolin-2(1H)-one (0.9 g, 64%) as a white solid. LCMS: RT 0.90 min. LCMS (ES-API), m/z 208.0 (M+H).

Workup

  1. extractionextracted with sat NaHCO3 solution and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customto afford a white solid
  5. customThe crude material was purified by silica gel flash chromatography (12 g, 40-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5fcff995a72f48ab809e1f45d45bf69d
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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