Pyridine → HCID 178497632, compound

HRID 127674Notes

Reaction equation

HRID 127674 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O)([O:3][CH3:4])=[O:2].O=S(Cl)Cl.N1C=CC=CC=1.[C:24]([NH:31][NH2:32])(=[O:30])/[CH:25]=[CH:26]\[C:27]([OH:29])=O>C(COC)OC.C(Cl)(Cl)Cl>[C:1]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([N:31]1[C:24](=[O:30])[CH:25]=[CH:26][C:27]([OH:29])=[N:32]1)=[O:9])([O:3][CH3:4])=[O:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 20392Monomethyl phthalateHCID 24386Thionyl ChlorideHCID 12898265(Z)-4-hydrazinyl-4-oxobut-2-enoic acid

Product 1

HCID 178497632HCID 178497632, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Into a 100 ml round-bottomed flask fitted with a stirrer and reflux condenser there was charged 10.8 g (0.06 mole) of 2-carbomethoxybenzoic acid and 50 ml of chloroform. There was then added 7.8 G (0.066 mole) of SOCl2, followed by refluxing for 2 hr. The chloroform was then removed by distillation, followed by addition of 50 ml. of dimethoxyethane, 4.7 g (0.06 mole) of pyridine and 6.7 g (0.06 mole) of maleic hydrazide. The mixture was allowed to stir over night. The resulting reaction mixture was filtered to remove solids. Then the product was precipitated from the filtrate by addition of water and was recovered as a solid by filtration. The solid material was washed with hexane-ether solvent mixture and was filtered and dried. The yield was 6.6 g, m.p. 144°-145° C. Infrared and nuclear magnetic resonance spectra were consistent with the structure of the compound as named above.

Workup

  1. customInto a 100 ml round-bottomed flask fitted with a stirrer
  2. temperaturereflux condenser
  3. temperatureby refluxing for 2 hr
  4. customThe chloroform was then removed by distillation
  5. additionfollowed by addition of 50 ml
  6. customThe resulting reaction mixture
  7. filtrationwas filtered
  8. customto remove solids
  9. customThen the product was precipitated from the filtrate by addition of water
  10. filtrationwas recovered as a solid by filtration
  11. washThe solid material was washed with hexane-ether solvent mixture
  12. filtrationwas filtered
  13. customdried

Sources & evidence

ORD record
ord-aae0653dcd0a4784b8f0b95a22ed7c42
Source dataset
uspto-grants-1981_03
Patent number
US04256884

Reaction notes

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