Hydrochloric Acid → HCID 70543312, compound

HRID 2285822Notes

Reaction equation

HRID 2285822 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][C:5]=1[Cl:11].[CH2:13]([NH2:16])[CH:14]=[CH2:15].C(=O)([O-])[O-].[Na+].[Na+].[ClH:23]>C(OCC)C.C(O)C>[OH2:2].[ClH:11].[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][C:5]=1[NH:16][CH2:13][CH:14]=[CH2:15].[CH2:13]([NH:16][C:5]1[N:6]=[C:7]([CH3:10])[CH:8]=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:12])[CH:14]=[CH2:15].[ClH:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7853AllylamineHCID 10340Sodium CarbonateHCID 13055804Methyl 2-chloro-6-methylpyridine-3-carboxylate

Product 1

HCID 70543312HCID 70543312, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherCatalystHCID 702EthanolSolvent2×

Procedure

A stirred mixture of 9.25 g. (0.05 mole) of methyl-2-chloro-6-methylnicotinate, 2.85 g. (0.05 mole) of allylamine and 5.3 g. (0.05 mole) of sodium carbonate in 50 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 diluted with 50 ml. of water and was extracted with 50 ml. of diethyl ether. The ether layer was dried over magnesium sulfate, filtered and was evaporated. The residue was passed through a neutral aluminum oxide column using ethyl acetate as the eluent. Evaporation of the ethyl acetate gave 3.1 g. of product. A small amount of this oil was dissolved in diethyl ether containing a few drops of ethanol and this solution was acidified with an ethereal hydrochloric acid solution. The precipitate which formed was collected and was recrystallized from ethyl acetate to give 2-allylamino-6-methylnicotinic acid methyl ester hydrochloride hemihydrate, m.p. 140°-142° C.

Workup

  1. additionA stirred mixture of 9.25 g
  2. temperatureunder reflux for 5 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated in a rotary evaporator
  5. additionThe residue was diluted with 50 ml
  6. extractionof water and was extracted with 50 ml
  7. dry with materialThe ether layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. customwas evaporated
  10. customEvaporation of the ethyl acetate
  11. customgave 3.1 g
  12. customThe precipitate which formed
  13. customwas collected
  14. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b56ba0a8c3ac401882523d6fcb5248b6
Source dataset
uspto-grants-1982_04
Patent number
US04324893

Reaction notes

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