Quinoline → 4-Cyano-3-nitrobenzoic acid

HRID 266857노트

반응식

HRID 266857 반응식
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[N:14]1C2C(=CC=CC=2)C=C[CH:15]=1>Cl.O>[C:15]([C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12])#[N:14]

참가 물질

5

반응물 2

HCID 7047QuinolineHCID 73204-Chloro-3-nitrobenzoic acid

생성물 1

HCID 221685834-Cyano-3-nitrobenzoic acid수율 48%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 962Water용매

실험 절차

4-Chloro-3-nitrobenzoic acid (5.84 g, 29 mM), cuprous cyanide (5.2 g, 58 mM), cuprous chloride (0.96 g, 9.7 mM), and quinoline (6.9 ml, 58 mM) were heated under an argon atmosphere at 180° for 3.5 hours. After cooling, the mixture was dissolved in concentrated hydrochloric acid (60 ml), diluted with water (80 ml), and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with aqueous NaH2PO4, brine, and dried over MgSO4. Crude product was purified by chromatography on silica, eluting with a mixture of dichloromethane/acetic acid (98:2), to give 4-cyano-3-nitrobenzoic acid (2.65 g, 48%). Nmr (DMSO-d6): δ 8.31 (d, 1H); 8.41 (dd, 1H); 8.68 (d, 1H).

후처리

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. washThe combined organic layers were washed with aqueous NaH2PO4, brine
  4. dry with materialdried over MgSO4
  5. customCrude product was purified by chromatography on silica
  6. washeluting with a mixture of dichloromethane/acetic acid (98:2)

출처 및 근거

ORD 기록
ord-f99ab914501d4c2ba4e8dc2de41b4a96
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05652233

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