Nitric Acid → 3-Acetoxy-4-(Acetylamino)-5-Nitrobenzoic Acid

HRID 1602800

反応式

HRID 1602800 の反応式
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[O:14][C:15](=[O:17])[CH3:16])(=[O:3])[CH3:2].CC(OC(C)=O)=O.[N+:25]([O-])([OH:27])=[O:26]>O1CCOCC1>[C:15]([O:14][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([N+:25]([O-:27])=[O:26])[C:5]=1[NH:4][C:1](=[O:3])[CH3:2])[C:9]([OH:11])=[O:10])(=[O:17])[CH3:16]

参加物

5

反応物 3

HCID 944Nitric AcidHCID 7918Acetic Anhydride2 回HCID 4938454-(Acetylamino)-3-acetoxybenzoic acid

生成物 1

HCID 4938463-Acetoxy-4-(Acetylamino)-5-Nitrobenzoic Acid収率 89.9%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
0 °C

実験手順

Compound 102 (1.00 g, 4.21 mmol) was suspended with stirring in a mixture of Ac2O (8.33 mL, 8.99 g, 88.2 mmol) and dioxane (6.6 mL). This was cooled to 0° C., and a cold solution of the nitrating mixture made from Ac2O (3.33 mL, 3.59 g, 35.2 mmol) and concentrated HNO3 (3.33 mL) was slowly added to the mixture containing 102. The reaction mixture was then warmed to 30-35° C. until the reaction was complete as evidenced by TLC. The reaction mixture was poured onto ice/water (100 mL), extracted with EtOAc (4×50 mL), dried (NaSO4), and concentrated to dryness on a rotary evaporator to give crude 104 (1.05 g, 89.9%) as an oil. Trituration with CHCl3 gave a solid: mp 196-201° C. (dioxane/hexane).

後処理

  1. additionwas slowly added to the mixture
  2. additioncontaining 102
  3. temperatureThe reaction mixture was then warmed to 30-35° C. until the reaction
  4. additionThe reaction mixture was poured onto ice/water (100 mL)
  5. extractionextracted with EtOAc (4×50 mL)
  6. dry with materialdried (NaSO4)
  7. concentrationconcentrated to dryness on a rotary evaporator

出典と根拠

ORDレコード
ord-ab628f2bfd6241b282ef57eece1e4f30
出典データセット
uspto-grants-1999_11
特許番号
US05985859

関連ノート

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