Hydrochloric Acid → 6-Chloro-3-iodo-2-methylpyridine

HRID 2276041ノート

反応式

HRID 2276041 の反応式
[ClH:1].[I:2][C:3]1[CH:4]=[CH:5][C:6](N)=[N:7][C:8]=1[CH3:9].N([O-])=O.[Na+]>O>[Cl:1][C:6]1[N:7]=[C:8]([CH3:9])[C:3]([I:2])=[CH:4][CH:5]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 9596135-Iodo-6-methylpyridin-2-amineHCID 23668193Sodium Nitrite

生成物 1

HCID 425530566-Chloro-3-iodo-2-methylpyridine収率 30%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a stirred solution of concentrated hydrochloride acid (233 mL) at 0° C. was added 5-iodo-6-methyl-pyridin-2-ylamine (25 g, 107 mmol, 1 eq) followed by addition of pre-dissolved sodium nitrite (29.5 g, 427 mmol, 4 eq) in water (150 mL) in drop wise manner over period of 30 minutes. Resulting reaction mixture was stirred at room temperature for 16 hours. After complete consumption of starting material, reaction mixture was cooled to 0° C., and pH was adjusted to 12 by saturated aqueous sodium hydroxide solution, extracted with DCM (3×200 mL). Combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to get brown oil (20 g, crude). Crude was purified by column chromatography using silica gel (100-200 mesh). Desired compound was eluted at 4% ethyl acetate in hexane to get title compound as brown oil (8 g, 30%). 1H NMR (400 MHz, CDCl3) δ: 2.69 (s, 3H), 6.88 (d, J=8.04 Hz, 1H), 7.95 (d, J=8.24 Hz, 1H). LC-MS (m/z): 254.0 (M+H).

後処理

  1. customResulting
  2. customreaction mixture
  3. customAfter complete consumption of starting material, reaction mixture
  4. temperaturewas cooled to 0° C.
  5. extractionextracted with DCM (3×200 mL)
  6. dry with materialCombined organic layer was dried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto get brown oil (20 g, crude)
  9. customCrude was purified by column chromatography
  10. washDesired compound was eluted at 4% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-a96fe047854b43f7a217fe4e619f0a02
出典データセット
uspto-grants-2015_09
特許番号
US09131697B2

反応ノート

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