Oxalyl chloride → HCID 20343795, compound

HRID 2049558Notes

Reaction equation

HRID 2049558 reaction equation
[CH3:1][C:2]1([CH3:18])[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[C:19](Cl)(=[O:23])[C:20](Cl)=[O:21]>C(Cl)Cl>[CH3:1][C:2]1([CH3:18])[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4]3=[C:5]([C:19](=[O:23])[C:20](=[O:21])[N:3]13)[CH:6]=[CH:7][CH:8]=2

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 12523274HCID 12523274, compound

Product 1

HCID 20343795HCID 20343795, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1,2-dihydro-2,2-dimethyl-4-phenylquinoline (5.0 g., 21.2 mMole) in 50 ml. dry methylene chloride was added dropwise with stirring to oxalyl chloride (2.77 g., 22.0 mMole) in 200 ml. dry methylene chloride at 30° C. and protected from moisture. Addition required one hour, and when complete the orange solution was stirred 30 minutes at ambient temperature and two hours at reflux. The solvent was removed at reduced pressure and the purple-brown crystalline residue air dried. A single recrystallization from chloroform/60°-110° C. ligroine produced a solid 3.97 g. (63.5%) melting at 210.5°-212° C.

Workup

  1. customat 30° C.
  2. additionAddition required one hour, and when complete the orange solution
  3. temperatureat reflux
  4. customThe solvent was removed at reduced pressure
  5. customthe purple-brown crystalline residue air dried
  6. customA single recrystallization from chloroform/60°-110° C. ligroine

Sources & evidence

ORD record
ord-08cce10511e349ea8d2fb1c82569966d
Source dataset
uspto-grants-1980_04
Patent number
US04198414

Reaction notes

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