Methanol → Methyl cinnoline-4-carboxylate

HRID 255851Notes

Reaction equation

HRID 255851 reaction equation
[C:1](Cl)(=O)C(Cl)=O.[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([O-:19])=[O:18])=[CH:9][N:8]=1.[K+].N1C=CC=CC=1.CO>C1(C)C=CC=CC=1>[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([O:19][CH3:1])=[O:18])=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 65578Oxalyl chlorideHCID 23713893HCID 23713893, compound

Product 1

HCID 13958988Methyl cinnoline-4-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 0.64 g of oxalyl chloride in 5 ml of dry toluene was added over 5 minutes to a stirred suspension of 0.98 g of 2 in 10 ml of dry toluene, at 0° C. The resulting mixture was stirred for 20 minutes at 0° C., for 30 minutes at room temperature, and for one hour at 80° C. The mixture was cooled and added in portions over 5 minutes to a stirred ice cold mixture of 0.4 g of pyridine, 0.32 g of methanol and 10 ml of dry toluene. The resulting mixture was held overnight at room temperature, then stripped in a rotary evaporator, and the residue was chromatographed over silica gel, using 5% ethyl acetate/methylene chloride mixture as eluent, to give 4, as yellow crystals, m.p.: 57°-58° C.

Workup

  1. waitfor one hour at 80° C
  2. temperatureThe mixture was cooled
  3. waitThe resulting mixture was held overnight at room temperature
  4. customstripped in a rotary evaporator
  5. customthe residue was chromatographed over silica gel
  6. customto give 4

Sources & evidence

ORD record
ord-f0a4d82c46134429b5b051167be141a4
Source dataset
uspto-grants-1987_10
Patent number
US04699651

Reaction notes

Loading…