Hydrochloric Acid → Methyl 5-amino-6-chloropyridine-3-carboxylate

HRID 50333

反応式

HRID 50333 の反応式
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.O.Cl>C(O)C.[Fe]>[NH2:12][C:11]1[C:2]([Cl:1])=[N:3][CH:4]=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7]

参加物

6

反応物 3

HCID 313Hydrochloric Acid2 回HCID 962Water2 回HCID 346961Methyl 6-chloro-5-nitronicotinate

生成物 1

HCID 18412438Methyl 5-amino-6-chloropyridine-3-carboxylate

試薬・触媒・溶媒 2

HCID 23925Iron触媒2 回HCID 702Ethanol溶媒

実験手順

A solution of 1.08 g (5.00 mmol) of methyl 6-chloro-5-nitronicotinate (see A. H. Berrie, G. T. Newbold, and F. S. Spring in J. Chem. Soc., 2590, 1951) in 25 mL of absolute ethanol was mixed successively with 0.53 mL (29 mmol) of water, 3.2 g (57 mmol) of iron powder and 0.030 mL of concentrated hydrochloric acid and heated to boiling for one hour. Then equal quantities of water, iron powder and hydrochloric acid were added and the mixture was heated to boiling for 30 minutes. The precipitate formed on cooling was filtered off and washed with ethanol and the solvent was distilled off in vacuo. Yield: 0.75 g (81% of theory) of greenish-yellow solid, C7H7ClN2O2 (186.60); Rf value: 0.31 (silica gel; ethyl acetate/petroleum ether=1:4); YEF-Mass spectrum: M+=186 and 188 (chlorine isotopes).

後処理

  1. temperatureheated
  2. temperaturethe mixture was heated
  3. waitto boiling for 30 minutes
  4. customThe precipitate formed
  5. temperatureon cooling
  6. filtrationwas filtered off
  7. washwashed with ethanol
  8. distillationthe solvent was distilled off in vacuo

出典と根拠

ORDレコード
ord-5a3642bc30304728b7aadefe8ca48501
出典データセット
uspto-grants-2004_03
特許番号
US06710055B2

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