Hydrochloric Acid → 2-Allylamino-6-methylnicotinic acid methyl ester

HRID 2058183

反応式

HRID 2058183 の反応式
Cl[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])[CH:14]=[CH2:15].C(=O)([O-])[O-].[Na+].[Na+].Cl>C(OCC)C.C(O)C>[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][CH:14]=[CH2:15]

参加物

7

反応物 4

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

生成物 1

HCID 128186562-Allylamino-6-methylnicotinic acid methyl ester

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether触媒HCID 702Ethanol溶媒2 回

実験手順

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, m.p. 140°-2° C.

後処理

  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

出典と根拠

ORDレコード
ord-810224417b354735ba82b7500626e8b1
出典データセット
uspto-grants-1980_07
特許番号
US04215123

関連ノート

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