Water → 5-Methoxyisoquinoline

HRID 1066860Notes

Reaction equation

HRID 1066860 reaction equation
O[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[CH2:32][O:33]C(/N=N/C(OCC)=O)=O.O>C1COCC1>[CH3:32][O:33][C:3]1[CH:2]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[CH:8]2

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 135441757Quinolin-5-ol

Product 1

HCID 137542835-Methoxyisoquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an oven dry three neck flask was added 5-hydroxy-quinoline (5 g, 34.5 mmol), and triphenylphosphine. The solids were dissolved in THF (100 mL) and DEAD (8.19 mL, 51.7 mmol) was added slowly. The maroon reaction mixture was stirred at room temperature overnight and then poured into H2O (100 mL) and extracted into EtOAc (3×150 mL). The combined organic fractions were dried over Na2SO4, filtered, concentrated, and purified by column chromatography using 20% EtOAc/hexanes as the eluent. The title compound was isolated as 3.5 g (64%) of a white solid.

Workup

  1. customTo an oven dry three neck flask
  2. customThe maroon reaction mixture
  3. extractionextracted into EtOAc (3×150 mL)
  4. dry with materialThe combined organic fractions were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-d78d3da38d534e11a1fed98a079a03e0
Source dataset
uspto-grants-2001_06
Patent number
US06245780B1

Reaction notes

Loading…