Acetic Anhydride → HCID 178418479, compound

HRID 64675Notes

Reaction equation

HRID 64675 reaction equation
C(OC(=O)C)(=[O:3])C.CCN(CC)CC.[N+:15]1([O-])[C:16](=[CH:20][CH:21]=[C:22]([CH:26]=1)[C:23]([OH:25])=[O:24])C(O)=O>C(Cl)(Cl)(Cl)Cl>[OH:3][C:16]1[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:26][N:15]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 136435031-Oxo-1lambda~5~-pyridine-2,5-dicarboxylic acid

Product 1

HCID 178418479HCID 178418479, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

20.4 g of acetic acid anhydride (0.2 mole), 20.2 g of Et3N (0.2 mole) and 50 ml of CCl4 were put up in a flask. 18.3 g of isocinchomeronic acid-N-oxide (0.1 mole) was added by portions to this solution. The temperature rose to 50° C. After completion of the reaction the solvents were distilled off. About 100 ml of 20 percent KOH was added drop by drop to the viscous residue and the acetate was saponified over a 15 minute period at 80° C. After removal of the Et3N by extraction, the aqueous solution was acidified with concentrated HCl. The precipitate was sucked off, washed with water and dried under a vacuum. 11.0 g of 6-hydroxy nicotinic acid was obtained, which was pure according to NMR. The crude yield was about 79 percent.

Workup

  1. customrose to 50° C
  2. customAfter completion of the reaction the solvents
  3. distillationwere distilled off
  4. additionAbout 100 ml of 20 percent KOH was added drop by drop to the viscous residue
  5. customAfter removal of the Et3N
  6. extractionby extraction
  7. washwashed with water
  8. customdried under a vacuum

Sources & evidence

ORD record
ord-52e57b3012044058a486db30d64d6456
Source dataset
uspto-grants-1986_09
Patent number
US04609734

Reaction notes

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