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

HRID 1713121노트

반응식

HRID 1713121 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

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

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-12aaf4a0636f440e82c01448b9de6369
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795262B2

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