Oxalyl chloride → HCID 15157732, compound

HRID 892736Notes

Reaction equation

HRID 892736 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[NH:7]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][CH:15]=2)[CH2:10][CH2:9][CH2:8]1>O1CCCC1>[O:3]=[C:2]1[C:15]2=[C:16]3[C:11](=[CH:12][C:13]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14]2)[CH2:10][CH2:9][CH2:8][N:7]3[C:1]1=[O:5]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 15232657HCID 15232657, compound

Product 1

HCID 15157732HCID 15157732, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the refluxing mixture of oxalyl chloride (0.3 ml) in dry tetrahydrofuran (THF; 15 ml) was added ethyl 1,2,3,4-tetrahydroquinolin-6-ylacetate (500 mg) in dry THF (5 ml) dropwise. The mixture was refluxed for 4 hours after addition was completed, then cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in carbon disulfide (20 ml) and added aluminum chloride (610 mg) portionwise. The mixture was refluxed for 4 hours and allowed to stand for overnight at room temperature. After decantation of the solvent, ice water (20 ml) was added to the residue. The mixture was extracted with chloroform and dried over anhydrous sodium sulfate. Evaporation of chloroform afforded the title compound. The compound was recrystallized from acetonitrile to give 490 mg (75%) of dark red needles, mp 124°-125° C.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. additionafter addition
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in carbon disulfide (20 ml)
  5. additionadded aluminum chloride (610 mg) portionwise
  6. temperatureThe mixture was refluxed for 4 hours
  7. additionAfter decantation of the solvent, ice water (20 ml) was added to the residue
  8. extractionThe mixture was extracted with chloroform
  9. dry with materialdried over anhydrous sodium sulfate
  10. customEvaporation of chloroform

Sources & evidence

ORD record
ord-c027b3e1bd7345dfbce84ffa14b1e145
Source dataset
uspto-grants-1992_06
Patent number
US05120743

Reaction notes

Loading…