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

HRID 1713121Notes

Reaction equation

HRID 1713121 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-12aaf4a0636f440e82c01448b9de6369
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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