3-Chloroaniline → HCID 12588336, 화합물

HRID 242985노트

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HRID 242985 반응식
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:11][C:12]1[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:11][C:12]1[CH:13]=[C:14]([NH:18][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:15]=[CH:16][CH:17]=1

참가 물질

5

반응물 3

HCID 79323-ChloroanilineHCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridine

생성물 1

HCID 12588336HCID 12588336, 화합물수율 22.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
140 °C

실험 절차

A mixture of 2-chloro-3-nitropyridine (317 mg, 2.0 mmol), 3-chlorophenylamine (0.212 mL, 2.0 mmol) and potassium carbonate (829 mg, 6.0 mmol) in DMF (3 mL) was heated at 140° C. for 30 min using microwave irradiation. After cooling to RT, the reaction mixture was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc (×3) and the combined organic fractions were washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting brown oil (370 mg) was purified by column chromatography (Si—PCC, gradient 0-100% DCM in cyclohexane) to afford the title compound as a red solid (111 mg, 22%). LCMS (Method B): RT 3.95 min [M+H]+ 250.0.

후처리

  1. custommicrowave irradiation
  2. temperatureAfter cooling to RT
  3. customthe reaction mixture was partitioned between EtOAc and water
  4. extractionThe aqueous phase was extracted with EtOAc (×3)
  5. washthe combined organic fractions were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting brown oil (370 mg) was purified by column chromatography (Si—PCC, gradient 0-100% DCM in cyclohexane)

출처 및 근거

ORD 기록
ord-5ee833ae4df74ed38a2c01c08772423c
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653089B2

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