Phosphorus oxychloride → HCID 86681525, compound

HRID 2361375Notes

Reaction equation

HRID 2361375 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[C:18]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[C:20]=4[CH3:28])=[N:17][NH:16][C:15](=O)[C:11]=3[NH:12][C:13]=2[CH:14]=1.P(Cl)(Cl)([Cl:32])=O>>[Cl:32][C:15]1[C:11]2[NH:12][C:13]3[CH:14]=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:7]=[CH:8][C:9]=3[C:10]=2[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[C:20]=2[CH3:28])=[N:17][N:16]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136359794HCID 136359794, compound

Product 1

HCID 86681525HCID 86681525, compoundYield 80.5%

Procedure

A yellow, homogeneous solution of 7-(2-methoxyethoxy)-1-(2-methyl-3-nitrophenyl)-3H-pyridazino[4,5-b]indol-4(5H)-one (0.2510 g, 0.636 mmol) in phosphoryl trichloride (20 mL, 0.636 mmol) under nitrogen was heated at 100° C. After 1 h, the reaction was cooled to room temperature and concentrated in vacuo. The residue was dissolved in cold EtOAc (250 mL) and was with ice-cold water (40 mL), ice-cold saturated aqueous NaHCO3 (40 mL), ice-cold water (40 mL) and ice-cold brine (40 mL), successively. The organic solution was dried over MgSO4 and concentrated in vacuo to give the desired product (0.2115 g, 0.512 mmol, 80% yield) as a light orange solid.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in cold EtOAc (250 mL)
  3. dry with materialThe organic solution was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c9434822903f4e0997c984497ac05ede
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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