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

HRID 427521ノート

反応式

HRID 427521 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c59e449a55fc4cd4853fe91be4e4215e
出典データセット
uspto-grants-2001_11
特許番号
US06313137B1

反応ノート

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