Phosphorus oxychloride → 6-Benzyl-2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine

HRID 1713121ノート

反応式

HRID 1713121 の反応式
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[NH:14][C:13](=O)[CH:12]=[CH:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:21]>>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]([Cl:21])[CH:12]=[CH:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 223351456-Benzyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one

生成物 1

HCID 162287476-Benzyl-2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine

反応条件

温度
100 °C

実験手順

To POCl3 (20 mL) is added 6-benzyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one (1.21 g, 5.04 mmol) and the mixture is heated at 100° C. for 6 hr. Solvent is removed and the thick oil is poured onto crashed ice (60 g). Upon stirring, solid Na2CO3 is added to the suspension until pH>7. EtOAc (60 ml) is added and the layers are separated. The aqueous layer is extracted with EtOAc (30 ml) and the combined extracts are dried and evaporated. The residue is purified by flash silica gel column eluting with hexane/EtOAc (4:1) to give the title compound as a light yellow solid. MS (M+1): 259.1.

後処理

  1. customSolvent is removed
  2. additionthe thick oil is poured
  3. additionsolid Na2CO3 is added to the suspension until pH>7
  4. additionEtOAc (60 ml) is added
  5. customthe layers are separated
  6. extractionThe aqueous layer is extracted with EtOAc (30 ml)
  7. customthe combined extracts are dried
  8. customevaporated
  9. customThe residue is purified by flash silica gel column
  10. washeluting with hexane/EtOAc (4:1)

出典と根拠

ORDレコード
ord-12aaf4a0636f440e82c01448b9de6369
出典データセット
uspto-grants-2010_09
特許番号
US07795262B2

反応ノート

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