Diisopropylamine → 2-Ethyl-6-methylbenzyl 5-(2-ethyl-6-methylbenzyloxy)-6-nitronicotinate

HRID 427521노트

반응식

HRID 427521 반응식
[OH:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:14]([C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:17]=1[CH2:18]Cl)[CH3:15].C(N[CH:29]([CH3:31])[CH3:30])(C)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[CH2:14]([C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:17]=1[CH2:18][O:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O:9][CH2:21][C:20]1[C:17]([CH3:18])=[CH:16][CH:14]=[CH:15][C:31]=1[CH2:29][CH3:30])=[O:8])[CH3:15]

참가 물질

6

반응물 3

HCID 7912DiisopropylamineHCID 121489182-Ethyl-6-methylbenzyl chlorideHCID 183574395-Hydroxy-6-nitronicotinic acid

생성물 1

HCID 536818842-Ethyl-6-methylbenzyl 5-(2-ethyl-6-methylbenzyloxy)-6-nitronicotinate수율 31.2%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6342Acetonitrile용매

실험 절차

5-hydroxy-6-nitronicotinic acid (1 g, 5 mmol), 2-ethyl-6-methylbenzylchloride (1.85 g, 11 mmol), N,N-diisopropylamine (1.75 g, 14 mmol) and tetrabutylammonium iodide (0.1 g) was added to acetonitrile (10 ml) and was refluxed for 3 h. The solvent was evaporated under reduced pressure and the residue was solved in methylene chloride and washed with water. The organic layer was separated , dried and evaporated under reduced pressure. Purification of the residue by column chromatograhy on silica gel using n-hexane:methylene chloride (1:1) as eluent gave 0.7 g (29%) of the title compound.

후처리

  1. temperaturewas refluxed for 3 h
  2. customThe solvent was evaporated under reduced pressure
  3. washwashed with water
  4. customThe organic layer was separated
  5. customdried
  6. customevaporated under reduced pressure
  7. customPurification of the residue by column chromatograhy on silica gel

출처 및 근거

ORD 기록
ord-c59e449a55fc4cd4853fe91be4e4215e
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313137B1

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