Hydrochloric Acid → 5-tert-butyl-3-nitro-1H-pyrrole-2-carboxylic acid

HRID 18932ノート

反応式

HRID 18932 の反応式
[C:1]([C:5]1[NH:9][C:8]([C:10]([O:12]C)=[O:11])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl>O.C1COCC1.CO>[C:1]([C:5]1[NH:9][C:8]([C:10]([OH:12])=[O:11])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 18322358methyl 5-tert-butyl-3-nitro-1H-pyrrole-2-carboxylate

生成物 1

HCID 183223915-tert-butyl-3-nitro-1H-pyrrole-2-carboxylic acid収率 64.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21899815MeOH tetrahydrofuran溶媒

反応条件

温度
75 °C

実験手順

A solution of LiOH monohydrate (0.083 g, 2.0 mmol) in water (1 mL) was added to a solution of methyl 5-tert-butyl-3-nitro-1H-pyrrole-2-carboxylate (0.150 mL, 0.66 mmol) in THF:MeOH (3:1, 3 mL) and the resulting mixture heated at 75° C. for 5 hours. The reaction was cooled down to room temperature and acidified with 1N aqueous HCl, extracted with ethyl acetate. The combined organic layers were dried, the solvent eliminated under vacuum and the crude product recrystallized from dichloromethane:hexane to afford 90 mg of expected 5-tert-butyl-3-nitro-1H-pyrrole-2-carboxylic acid as a yellow solid.

後処理

  1. temperatureThe reaction was cooled down to room temperature
  2. extractionextracted with ethyl acetate
  3. customThe combined organic layers were dried
  4. customthe crude product recrystallized from dichloromethane

出典と根拠

ORDレコード
ord-7453776a39e54e01a5ebd772ea3e57f2
出典データセット
uspto-grants-2010_06
特許番号
US07741479B2

反応ノート

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