Phosphorus oxychloride → HCID 77230217, compound

HRID 729535Notes

Reaction equation

HRID 729535 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:17]=[C:16](O)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.O=P(Cl)(Cl)[Cl:21].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:21][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychloride2×HCID 81531DiisopropylethylamineHCID 178515690HCID 178515690, compound

Product 1

HCID 77230217HCID 77230217, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 250 mL RBF was added 4.6 g (18 mmol) 2-(2-chloro-pyridin-4-yl)-quinolin-4-ol and 100 mL POCl3, and the mixture was treated with 3.1 mL DIEA (18 mmol). The mixture was was stirred at rt for 1 h, and all starting material was converted. All POCl3 was vacuumed down. The residue was dissolved in 250 mL DCM, washed with saturated NaHCO3 carefully to pH 8. The organic phase was dried over Na2SO4, concentrated and purified by column and yielded pale yellow 4-chloro-2-(2-chloro-pyridin-4-yl)-quinoline. MS (ES+): 275 (M+H)+.

Workup

  1. washwashed with saturated NaHCO3 carefully to pH 8
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by column

Sources & evidence

ORD record
ord-6e58e6483a9f4859a20f7405c89c5af7
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

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