Naphthalene → 5-Chloro-pyridine-3-carbaldehyde

HRID 1728189ノート

反応式

HRID 1728189 の反応式
C1(OC([N:10]2[CH:15]=[C:14]([CH:16]=[O:17])[CH:13]=[C:12]([Cl:18])[CH2:11]2)=O)C=CC=CC=1.[S].C1C2C(=CC=CC=2)C=CC=1>C(OCC)C>[Cl:18][C:12]1[CH:13]=[C:14]([CH:16]=[O:17])[CH:15]=[N:10][CH:11]=1

参加物

5

反応物 3

HCID 931NaphthaleneHCID 5362487SulfurHCID 575659313-chloro-5-formyl-2H-pyridine-1-carboxylic acid phenyl ester

生成物 1

HCID 144441965-Chloro-pyridine-3-carbaldehyde

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

The mixture of 3-chloro-5-formyl-2H-pyridine-1-carboxylic acid phenyl ester (2.3 g, 8.8 mmol), sublimed sulfur (0.29 g, 9 mmol) and naphthalene (6 g) was refluxed under an argon atmosphere for 2 h. After the reaction was complete, the mixture was cooled to r.t., dissolved in ethyl ether (30 mL), and extracted with aqueous 10% HCl. The combined acid extracts were washed with ethyl ether (20 mL) and cooled to 0° C. Dichloromethane (30 mL) was added and “pH” of the mixture was adjusted to be basic with 25% aqueous NaOH, and the mixture was extracted with dichloromethane (20 mL). The combined organic phase was washed with brine, dried over K2CO3, filtered, and concentrated to give a brown solid. (0.8 g, 76%).

後処理

  1. temperaturewas refluxed under an argon atmosphere for 2 h
  2. extractionextracted with aqueous 10% HCl
  3. washThe combined acid extracts were washed with ethyl ether (20 mL)
  4. temperaturecooled to 0° C
  5. additionDichloromethane (30 mL) was added
  6. extractionthe mixture was extracted with dichloromethane (20 mL)
  7. washThe combined organic phase was washed with brine
  8. dry with materialdried over K2CO3
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a brown solid

出典と根拠

ORDレコード
ord-58e86f768a244136a67dc6224cf5b5d3
出典データセット
uspto-grants-2009_02
特許番号
US07495007B2

反応ノート

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