Ethyl chloroformate → HCID 12298145, compound

HRID 1973794Notes

Reaction equation

HRID 1973794 reaction equation
[NH:1]([C:8]1([C:14]([OH:16])=[O:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[OH-].[Na+].Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22]>O1CCCC1>[NH:1]([C:8]1([C:14]([OH:16])=[O:15])[CH2:9][CH2:10][N:11]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 12298144HCID 12298144, compound

Product 1

HCID 12298145HCID 12298145, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred and cooled (ice-salt bath) mixture of 12.1 parts of 4-anilinoisonipecotic acid, sodium salt, 200 parts of sodium hydroxide solution 1N and 20 parts of tetrahydrofuran are added dropwise 6.45 parts of ethyl chloroformate in 25 parts of tetrahydrofuran over 15 minutes and at a temperature between 2° and 5° C. Upon completion, stirring is continued for 3 hours in the cool-bath. The whole is extracted with ether. The aqueous phase is separated and degassed on a rotavapor without heating. The mixture is acidified with glacial acetic acid, whereupon an oil is separated. The latter is stirred in fresh water and extracted with chloroform. The extract is washed three times with water, dried, filtered and evaporated. The residue is crystallized from a mixture of ethyl acetate and petroleumether, yielding 4-anilino-1-(ethoxycarbonyl)isonipecotic acid; mp. 149°-156° C.

Workup

  1. temperaturecooled
  2. customat a temperature between 2° and 5° C
  3. stirringUpon completion, stirring
  4. extractionThe whole is extracted with ether
  5. customThe aqueous phase is separated
  6. customdegassed on a rotavapor
  7. temperaturewithout heating
  8. customis separated
  9. stirringThe latter is stirred in fresh water
  10. extractionextracted with chloroform
  11. washThe extract is washed three times with water
  12. customdried
  13. filtrationfiltered
  14. customevaporated
  15. customThe residue is crystallized from a mixture of ethyl acetate and petroleumether

Sources & evidence

ORD record
ord-b219d9a4cd564f80a55c08fabf73b765
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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