Phosphorus oxychloride → HCID 69661784, compound

HRID 2121583Notes

Reaction equation

HRID 2121583 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4](O)[C:5]2[N:13]3[C:8]([C:9]([C:14]4[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=4[CH3:22])=[CH:10][CH:11]=[CH:12]3)=[CH:7][C:6]=2[N:23]=1.OC1C2N3C(C=CC=C3)=C(C3C(C)=CC(C)=CC=3C)C=2N=C(C)C=1.P(Cl)(Cl)([Cl:51])=O>>[Cl:51][C:4]1[C:5]2[N:13]3[C:8]([C:9]([C:14]4[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=4[CH3:22])=[CH:10][CH:11]=[CH:12]3)=[CH:7][C:6]=2[N:23]=[C:2]([CH3:1])[CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178424433HCID 178424433, compound

Product 1

HCID 69661784HCID 69661784, compound

Procedure

Heat at 100° C. for 1 h a solution of 4-hydroxy-2-methyl-10-(2,4,6-trimethylphenyl)pyridino-[2,3-b]indolizine 2-methyl-9-(2,4,6-trimethylphenyl)pyrido[2,3-b]-indolizin-4-ol (10.1 g; 32 mmol) in phosphorus oxychloride (60 mL), cool to ambient temperature, and concentrate in vacuo. Partition the residue into ice water and CH2Cl2. Separate the aqueous phase, extract twice with CH2Cl2, and wash the combined organic extracts with a 1 N aqueous sodium hydroxide solution and then with water. Dry the solution over Na2SO4, filter, and concentrate in vacuo. Filter the dark residue through a short pad of silica gel and wash with 25% EtOAc in hexane. Concentrate the filtrate in vacuo to obtain the title compound as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 2.00 (s, 6H), 2.37 (s, 3H), 2.64 (s, 3H), 6.58 (t, 1H), 6.95 (dd, 1H), 7.00 (s, 2H), 7.07 (s, 1H), 7.08 (d, 1H), 9.26 (d, 1H).

Workup

  1. concentrationconcentrate in vacuo
  2. customPartition the residue into ice water and CH2Cl2
  3. customSeparate the aqueous phase
  4. extractionextract twice with CH2Cl2
  5. washwash the combined organic extracts with a 1 N aqueous sodium hydroxide solution
  6. dry with materialDry the solution over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. filtrationFilter the dark residue through a short pad of silica gel
  10. washwash with 25% EtOAc in hexane
  11. concentrationConcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-4bd9ec5cb8394026b4ed81ae211a6ceb
Source dataset
uspto-grants-2004_02
Patent number
US06696445B2

Reaction notes

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