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

HRID 50333

반응식

HRID 50333 반응식
[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]

참가 물질

6

반응물 3

HCID 313Hydrochloric Acid2회HCID 962Water2회HCID 346961Methyl 6-chloro-5-nitronicotinate

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매2회HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5a3642bc30304728b7aadefe8ca48501
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710055B2

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