Ethylene Glycol → 1(2H)-Phthalazinone, 4-(4-morpholinyl)-

HRID 535477Notes

Reaction equation

HRID 535477 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][N:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(O)CO>CCOC(C)=O>[O:16]1[CH2:17][CH2:18][N:13]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:12])[NH:4][N:3]=2)[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 8083MorpholineHCID 27751424-chlorophthalazin-1(2H)-one

Product 1

HCID 126895281(2H)-Phthalazinone, 4-(4-morpholinyl)-Yield 48%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-chlorophthalazin-1-one (0.49 g, 2.7 mmol), morpholine (2.4 mL, 27 mmol), and ethylene glycol (1.5 mL) was microwaved at 190° C. for 1 hour, and 210° C. for 30 minutes, diluted with EtOAc, washed with sat NaHCO3 and water, concentrated, adsorbed onto silica, and chromatographed (30% EtOAc/DCM) to give 300.0 mg of product as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 12.13 (s, 1H), 8.27-8.20 (m, 1H), 8.00-7.79 (m, 3H), 3.86-3.77 (m, 4H), 3.07 (dd, J=10.2, 5.6, 4H).

Workup

  1. customwas microwaved at 190° C. for 1 hour
  2. washwashed
  3. concentrationconcentrated
  4. customchromatographed (30% EtOAc/DCM)

Sources & evidence

ORD record
ord-3890ec9bb18c4c64bf470b44af655dad
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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