Hydrochloric Acid → HCID 131711834, compound

HRID 2058181Notes

Reaction equation

HRID 2058181 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:13]([NH2:16])[CH2:14][CH3:15].C(=O)([O-])[O-].[Na+].[Na+].Cl>C(OCC)C.C(O)C>[ClH:1].[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][C:10]([CH3:12])=[N:11][C:2]=1[NH:16][CH2:13][CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7852PropylamineHCID 10340Sodium CarbonateHCID 13055804Methyl 2-chloro-6-methylpyridine-3-carboxylate

Product 1

HCID 131711834HCID 131711834, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A stirred mixture of 37.1 g. (0.2 mole) of methyl 2-chloro-6-methyl-nicotinate, 11.8 g. (0.02 mole) of propylamine and 21.2 g. (0.02 mole) of sodium carbonate in 200 ml. of ethanol was heated under reflux for 5 hours. The mixture was filtered and the filtrate was evaporated in a rotary evaporator. The residue was triturated with 200 ml. of water and was extracted with 100 ml. of diethyl ether. The ether layer was dried over magnesium sulfate, filtered and was evaporated to give 31 g. of an oil. A small amount of this oil was dissolved in diethyl ether and was acidified with an etheral hydrochloric acid solution. On cooling, the oil which separated crystallized to yield 6-methyl-2-propylaminonicotinic acid methyl ester, hydrochloride. The solid was collected and was recrystallized from ethyl acetate to give the analytical sample, m.p. 113°-15° C.

Workup

  1. additionA stirred mixture of 37.1 g
  2. temperatureunder reflux for 5 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated in a rotary evaporator
  5. customThe residue was triturated with 200 ml
  6. extractionof water and was extracted with 100 ml
  7. dry with materialThe ether layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. customwas evaporated
  10. customto give 31 g
  11. temperatureOn cooling
  12. customthe oil which separated
  13. customcrystallized

Sources & evidence

ORD record
ord-6d4674116b5e42609fc5abfed5af81d7
Source dataset
uspto-grants-1980_07
Patent number
US04215123

Reaction notes

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