Hydrazine hydrate (1:1) → 2-Hydrazinyl-3-methoxypyridine

HRID 1037306

反応式

HRID 1037306 の反応式
Cl[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.O.[NH2:11][NH2:12]>>[CH3:9][O:8][C:7]1[C:2]([NH:11][NH2:12])=[N:3][CH:4]=[CH:5][CH:6]=1

参加物

3

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 1042522-Chloro-3-methoxypyridine

生成物 1

HCID 185454042-Hydrazinyl-3-methoxypyridine収率 57%

実験手順

A stirred solution of 2-chloro-3-methoxypyridine (4.86 g, 33.8 mmol) in hydrazine hydrate (40 mL) was heated under reflux for 1.5 hours. After cooling to RT, the reaction mixture was evaporated to dryness. The resulting residue was partitioned between 10% MeOH in CHCl3 and 40% w/v aqueous potassium carbonate. The aqueous phase was isolated and extracted twice with 10% MeOH in CHCl3. The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (2.7 g, 57%) as a buff solid. 1H NMR (300 MHz, DMSO-d6): δ 7.65 (dd, J=5.1 and 1.3 Hz, 1H), 6.99 (dd, J=7.7 and 1.3 Hz, 1H) overlapped with 6.98 (br s, 1H), 6.56 (dd, J=7.6 and 5.1 Hz, 1H), 4.05 (br s, 2H), 3.76 (s, 3H). LCMS (Method A): RT=0.34 min, [M+H]+=140.

後処理

  1. temperatureunder reflux for 1.5 hours
  2. customthe reaction mixture was evaporated to dryness
  3. customThe resulting residue was partitioned between 10% MeOH in CHCl3 and 40%
  4. customThe aqueous phase was isolated
  5. extractionextracted twice with 10% MeOH in CHCl3
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-fad8e7e33a6a4d25a13b14c73d9f3da3
出典データセット
uspto-grants-2013_10
特許番号
US08546376B2

関連ノート

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