Pyridine → Methyl 1,4,5,7-tetrahydro-2-methyl-4-(2-methylphenyl)-5-oxofuro[3,4-b]pyridine-3-carboxylate

HRID 1285547ノート

反応式

HRID 1285547 の反応式
C1C=C[NH+]=CC=1.Br[Br-]Br.[CH3:10][C:11]1[NH:12][C:13]([CH3:32])=[C:14]([C:28]([O:30][CH3:31])=[O:29])[CH:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[C:16]=1[C:17]([O:19]C)=[O:18].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:32][C:13]1[NH:12][C:11]2[CH2:10][O:19][C:17](=[O:18])[C:16]=2[CH:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[C:14]=1[C:28]([O:30][CH3:31])=[O:29]

参加物

4

反応物 2

HCID 1049PyridineHCID 12640525HCID 12640525、化合物

生成物 1

HCID 13193765Methyl 1,4,5,7-tetrahydro-2-methyl-4-(2-methylphenyl)-5-oxofuro[3,4-b]pyridine-3-carboxylate収率 61.1%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

In an operation carried out in a manner similar to that described in the preceding example, 1.52 grams of 80 percent pyridinium bromide perbromide (3.81 millimoles) was added in one portion to a solution of 1.00 gram (3.17 millimoles) of dimethyl 2,6-dimethyl-4-(o-tolyl)-1,4-dihydropyridine-3,5-dicarboxylate and 0.40 milliliter of pyridine in 20 milliliters of dry chloroform cooled to 0° C. The mixture was stirred for 30 minutes at 0° C., then at reflux temperature for 1.5 hours. Thereafter, the mixture was cooled, washed successively with hydrochloric acid and brine, dried, subjected to reduced pressure to remove the solvent and to obtain as residue crude methyl 2-methyl-4-(o-tolyl)-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxylate product. The crude product was chromatographed on silica and eluted with 65 percent ethyl acetate--35 percent hexane to obtain 0.58 gram (61 percent yield) of white crystalline material which after recrystallizing from ethyl acetate-hexane and drying at 80° C./0.005 mm Hg for 17 hours had a melting point of 224°-225° C. and the following analyses:

後処理

  1. temperatureat reflux temperature for 1.5 hours
  2. temperatureThereafter, the mixture was cooled
  3. washwashed successively with hydrochloric acid and brine
  4. customdried
  5. customto remove the solvent
  6. customto obtain as residue crude methyl 2-methyl-4-(o-tolyl)-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxylate product
  7. customThe crude product was chromatographed on silica
  8. washeluted with 65 percent ethyl acetate--35 percent hexane

出典と根拠

ORDレコード
ord-b4ea088eeac2446daafb45077cc301f8
出典データセット
uspto-grants-1986_01
特許番号
US04567268

反応ノート

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