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

HRID 18932노트

반응식

HRID 18932 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 21899815MeOH tetrahydrofuran용매

반응 조건

온도
75 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7453776a39e54e01a5ebd772ea3e57f2
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741479B2

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