Ethyl bromopyruvate → 1,2-Dicarbethoxypyrrolo[1,2-c]quinazoline

HRID 65927ノート

反応式

HRID 65927 の反応式
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:12][CH:11]=1.C(=O)(O)[O-].[Na+]>CCO>[C:4]([C:3]1[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:13][N:12]2[C:2]=1[C:18]1[CH:17]=[CH:16][CH:15]=[CH:14][C:19]=1[N:10]=[CH:11]2)([O:6][CH2:7][CH3:8])=[O:5]

参加物

5

反応物 3

HCID 66144Ethyl bromopyruvateHCID 516892Sodium BicarbonateHCID 22756349Ethyl Quinazoline-4-acetate

生成物 1

HCID 227563371,2-Dicarbethoxypyrrolo[1,2-c]quinazoline

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of ethyl bromopyruvate (8.0 g, 0.1041 m) and ethyl 4-quinazolylacetate prepared according to the procedure of Elderfield and Serlin, J. Org. Chem. 16, 1669 (1951) (2.32 g, 0.011 m) in dry EtOH (250 ml) was heated at reflux for 24 hr. Sodium bicarbonate was added until effervescence ceased. A solid formed and this was filtered, washed well with H2O, and dried. The crude product (1.8 g) was chromatographed on 150 g of Silicar. The desired product was eluted with 3% EtOAc/benzene. Crystallization from MeOH afforded the desired product as a white solid; m.p. 125°-126° C.

後処理

  1. temperatureat reflux for 24 hr
  2. customA solid formed
  3. filtrationthis was filtered
  4. washwashed well with H2O
  5. customdried
  6. customThe crude product (1.8 g) was chromatographed on 150 g of Silicar
  7. washThe desired product was eluted with 3% EtOAc/benzene
  8. customCrystallization from MeOH

出典と根拠

ORDレコード
ord-a3ffbe93a90740d3a2e3f2287da1359f
出典データセット
uspto-grants-1978_12
特許番号
US04129653

反応ノート

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