Pyridine → HCID 12070973, compound

HRID 1729623Notes

Reaction equation

HRID 1729623 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:12])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].N1C=CC=CC=1.[C:19]([CH2:23][CH2:24][C:25](Cl)=[O:26])([O:21][CH3:22])=[O:20]>C1C=CC=CC=1>[C:19]([CH2:23][CH2:24][C:25]([NH:12][C:4]1[C:5](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:26])([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 80001Methyl 4-chloroanthranilate

Product 1

HCID 12070973HCID 12070973, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To the solution of 444 g of methyl 4-chloro-anthranilate in 1.3 lt of benzene and 199 ml of pyridine, that of 406 g of 3-carbomethoxy-propionyl chloride in 200 ml of benzene is added dropwise while stirring and cooling with ice. The mixture is stirred for 19 hours at room temperature, filtered and the filtrate evaporated. The combined residues are taken up in 3 lt of chloroform, the solution washed with water, 1 lt of N hydrochloric acid, 1 lt of 10% aqueous sodium bicarbonate and again with water, dried, filtered, evaporated and the residue recrystallized from acetonitrile, to yield the methyl N-(3-carbomethoxypropionyl)-4-chloroanthranilate melting at 80°-84°.

Workup

  1. temperaturecooling with ice
  2. stirringThe mixture is stirred for 19 hours at room temperature
  3. filtrationfiltered
  4. customthe filtrate evaporated
  5. washthe solution washed with water, 1 lt of N hydrochloric acid, 1 lt of 10% aqueous sodium bicarbonate and again with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customthe residue recrystallized from acetonitrile

Sources & evidence

ORD record
ord-585524c65953491bbeb2b94fe4c01807
Source dataset
uspto-grants-1976_11
Patent number
US03989689

Reaction notes

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