Hydrochloric Acid → HCID 70543312, compound

HRID 1703128Notes

Reaction equation

HRID 1703128 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-093d123a032a46b58b04bbcbb2adacd7
Source dataset
uspto-grants-1982_09
Patent number
US04350817

Reaction notes

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