Ethanol → 1-Chloro-4-ethoxyphthalazine

HRID 1852068Notes

Reaction equation

HRID 1852068 reaction equation
[Na].Cl[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([Cl:13])=[N:5][N:4]=1.[CH3:14][CH2:15][OH:16]>>[Cl:13][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([O:16][CH2:15][CH3:14])=[N:4][N:5]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 784901,4-DichlorophthalazineHCID 5360545Sodium

Product 1

HCID 212176601-Chloro-4-ethoxyphthalazine

Procedure

Sodium (33.8 mg, 1.470 mmol) was allowed to react with EtOH (10 mL), then 1,4-dichlorophthalazine (279 mg, 1.4 mmol) was added and the reaction mixture was refluxing for 30 min. The hot solution was filtered and evaporated. The crude product was purified by silica gel chromatography eluting with 20% ethyl acetate in hexane to give 200 mg of the crude product 1-chloro-4-ethoxyphthalazine. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.29-8.18 (m, 2H), 7.99-7.90 (m, 2H), 4.73 (q, J=7.1 Hz, 2H), 1.57 (t, J=7.2 Hz, 3H); MS: MS m/z 209.06 (M++1).

Workup

  1. temperaturethe reaction mixture was refluxing for 30 min
  2. filtrationThe hot solution was filtered
  3. customevaporated
  4. customThe crude product was purified by silica gel chromatography
  5. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ede7a9f42302493888ca5b8b8e5e4b34
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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