Phosphorus oxychloride → 1-Chloro-4-(4-methoxybenzyl)phthalazine

HRID 2361026Notes

Reaction equation

HRID 2361026 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=O)[NH:10][N:9]=2)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:23])=O>>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([Cl:23])=[N:10][N:9]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 123328504-(4-methoxybenzyl)phthalazin-1(2H)-one

Product 1

HCID 866141621-Chloro-4-(4-methoxybenzyl)phthalazine

Procedure

To 4-(4-methoxybenzyl)phthalazin-1(2H)-one (1.18 g, 4.43 mmol) was added phosphorus oxychloride (4.13 ml, 44.3 mmol). A water condenser was attached and the mixture was heated to reflux under a nitrogen atmosphere for 15 hours. The reaction was concentrated in vacuo, diluted with methylene chloride and ice water, then quenched with solid sodium bicarbonate until pH was basic and gas evolution ceased. The layers were separated and the organic layers were dried over sodium sulfate, filtered through a pad of silica gel using EtOAc and concentrated to yield 1-(4-methoxybenzyl)-4-chlorophthalazine as a light orange solid. MS m/z=285 [M+1]+. Calc'd for C16H13ClN2O: 284.75.

Workup

  1. customA water condenser was attached
  2. temperaturethe mixture was heated
  3. temperatureto reflux under a nitrogen atmosphere for 15 hours
  4. concentrationThe reaction was concentrated in vacuo
  5. additiondiluted with methylene chloride and ice water
  6. customquenched with solid sodium bicarbonate until pH
  7. customThe layers were separated
  8. dry with materialthe organic layers were dried over sodium sulfate
  9. filtrationfiltered through a pad of silica gel
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-092c9f83889e4b94bbb75d36202c1b07
Source dataset
uspto-grants-2014_04
Patent number
US08686155B2

Reaction notes

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