Phosphorus oxychloride → HCID 70914022, compound

HRID 2277432Notes

Reaction equation

HRID 2277432 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](O)=[C:8]([C:17]#[N:18])[C:7]1=[O:19])[CH3:2].O=P(Cl)(Cl)[Cl:22]>O>[Cl:22][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])[C:7](=[O:19])[C:8]=1[C:17]#[N:18]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 70914076HCID 70914076, compound

Product 1

HCID 70914022HCID 70914022, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 1-(2-Ethoxy-ethyl)-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carbonitrile (1 eq, 0,150 g, 0.58 mmole) was added POCl3 neat. The resulting solution was heated to 100° C. for 8 hours. Reaction mixture was added dropwise to water (20 mL) which had been heated to 80° C. then cooled to RT and extracted with ethyl acetate (25 mL×3). Combined, organic phase was Washed consecutively with water, brine before drying over sodium sulfate. Organic phase was evaporated and the residue was purified by flash chromatography to afford 4-Chloro-1-(2-ethoxy-ethyl)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile as a yellow solid (0.109 g, 68%. LCMS calc M+H 277, obs M+H 277).

Workup

  1. customReaction mixture
  2. temperaturehad been heated to 80° C.
  3. temperaturethen cooled to RT
  4. extractionextracted with ethyl acetate (25 mL×3)
  5. washorganic phase was Washed consecutively with water, brine
  6. dry with materialbefore drying over sodium sulfate
  7. customOrganic phase was evaporated
  8. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ad5ad7d0f21646f5ac738e128627f81e
Source dataset
uspto-grants-2015_09
Patent number
US09133164B2

Reaction notes

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