Iodoethane → 4-(3,5-Dichloro-pyridin-4-ylmethyl)-2-ethyl-7-methoxy-2H-phthalazin-1-one

HRID 2268856Notes

Reaction equation

HRID 2268856 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:22])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[C:12](=[O:21])[NH:11][N:10]=1.[H-].[Na+].[CH2:25](I)[CH3:26]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:22])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[C:12](=[O:21])[N:11]([CH2:25][CH3:26])[N:10]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 224827114-(3,5-Dichloro-pyridin-4-ylmethyl)-7-methoxy-2H-phthalazin-1-one

Product 1

HCID 183816764-(3,5-Dichloro-pyridin-4-ylmethyl)-2-ethyl-7-methoxy-2H-phthalazin-1-oneYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-(3,5-dichloro-pyridin-4-ylmethyl)-7-methoxy-2H-phthalazin-1-one (0.52 g, 1.55 mmoles), prepared as described in example 38, in DMF (10 ml) was added with NaH (0.057 g, 1.55 mmoles) and, after 1 hour, with ethyl iodide (0.125 ml, 1.55 mmoles). After 1 night the mixture was diluted with water (10 volumes) and extracted twice with ethyl acetate. The organic phase was anhydrified and concentrated to give a solid which was purified by flash chromatography (eluent: ethyl acetate/petrolatum 3:7). There was thus obtained 0.44 g of the title compound (yield: 78%). m.p.: 150.2-151.2° C.

Workup

  1. customprepared
  2. extractionextracted twice with ethyl acetate
  3. concentrationconcentrated
  4. customto give a solid which
  5. customwas purified by flash chromatography (eluent: ethyl acetate/petrolatum 3:7)

Sources & evidence

ORD record
ord-b89c244d43fb40e7b0eb7272043a391e
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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