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

HRID 227760ノート

反応式

HRID 227760 の反応式
[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

参加物

3

反応物 2

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e9cc029c0dec46f697c65f090c2ecad2
出典データセット
uspto-grants-2009_07
特許番号
US07560551B2

反応ノート

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