N,N-Diethylaniline → Methyl 2-Chloro-5-iodonicotinate

HRID 1199806노트

반응식

HRID 1199806 반응식
[I:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:5][NH:6][CH:7]=1.CCN(C1C=CC=CC=1)CC.P(Cl)(Cl)([Cl:25])=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C.O>[Cl:25][C:5]1[C:4]([C:8]([O:10][CH3:11])=[O:9])=[CH:3][C:2]([I:1])=[CH:7][N:6]=1

참가 물질

7

반응물 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 20073492Methyl 5-iodo-1,2-dihydro-3-pyridinecarboxylate

생성물 1

HCID 2764559Methyl 2-Chloro-5-iodonicotinate수율 52%

시약·촉매·용매 3

HCID 962Water촉매HCID 66133Benzyl triethylammonium chloride촉매HCID 6342Acetonitrile용매

실험 절차

To a mixture containing 2.0 g of methyl 5-iodo-1,2-dihydro-3-pyridinecarboxylate, 1.6 g of diethylaniline, 1.64 g of benzyltriethylammonium chloride and 3.6 ml of distilled phosphorus oxychloride in 100 ml of dry acetonitrile are added 15 drops of water. The mixture is heated under reflux for 18 hours. After cooling the reaction mixture to room temperature, the solvent is removed under reduced pressure and the residue taken up in methylene chloride and extracted with water. The organic solution is dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on a column of flash silica gel using methylene chloride as the eluent. Evaporation of the eluent yields a pale yellowish solid which is recrystallized from aqueous ethanol to give 1.1 g (52%) of methyl 2-chloro-5-iodo-3-pyridinecarboxylate as a white solid: m.p. 73°-73.5° C.; NMR (80 MHz, CDCl3) delta 3.96 (s, 3H), 8.43 (d, 1H, J= 2.3 Hz), 8.71 (d, 1H, J=2.3 Hz).

후처리

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 18 hours
  3. customthe solvent is removed under reduced pressure
  4. extractionextracted with water
  5. dry with materialThe organic solution is dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is chromatographed on a column of flash silica gel
  8. customEvaporation of the eluent
  9. customyields a pale yellowish solid which
  10. customis recrystallized from aqueous ethanol

출처 및 근거

ORD 기록
ord-4dd813f9e0e64cc49d5963822b11a32e
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04902796

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