Phosphorus oxychloride → 6-Chloro-5-nitropyridine-3-carboxylic acid

HRID 392979ノート

反応式

HRID 392979 の反応式
O[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178524776HCID 178524776、化合物

生成物 1

HCID 3464596-Chloro-5-nitropyridine-3-carboxylic acid収率 95%

反応条件

温度
105 °C

実験手順

A suspension of 6-hydroxy-5-nitronicotinic acid (8 g, 43.5 mmol) (prepared by literature nitration of 6-hydroxynicotinic acid) in phosphorus oxychloride (24.3 mL, 261.0 mmol) was heated to reflux (105° C.) for 3 h under a nitrogen atmosphere. At the end of this time period all of the solids had dissolved. The reaction was cooled to rt and poured over 500 mL crushed ice, and stirring was continued for 30 minutes until all of the ice had melted. The aqueous mixture was extracted with a 1:2 mixture of THF in diethyl ether (3×150 mL). The pooled organic extracts were washed with brine (1×), dried (MgSO4), and concentrated on a rotary evaporator to afford intermediate 56 as a light brown solid (8.37 g, 95%). ESI-MS m/e 405.3 (2M−1).

後処理

  1. temperaturewas heated
  2. dissolutionAt the end of this time period all of the solids had dissolved
  3. temperatureThe reaction was cooled to rt
  4. additionpoured over 500 mL
  5. customcrushed ice
  6. extractionThe aqueous mixture was extracted with a 1:2 mixture of THF in diethyl ether (3×150 mL)
  7. washThe pooled organic extracts were washed with brine (1×)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated on a rotary evaporator

出典と根拠

ORDレコード
ord-ec3793ece9c84de2a742898b2a7e34a1
出典データセット
uspto-grants-2004_10
特許番号
US06803374B2

反応ノート

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