Formaldehyde → 5-(5-Nitroindol-3-ylmethyl)-2,2-dimethyl-1,3-dioxane4,6-dione

HRID 1647788

반응식

HRID 1647788 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[CH3:13][C:14]1([CH3:22])[O:21][C:19](=[O:20])[CH2:18][C:16](=[O:17])[O:15]1.C=O.N1CCC[C@H:26]1C(O)=O>C(#N)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:26][CH:18]1[C:19](=[O:20])[O:21][C:14]([CH3:22])([CH3:13])[O:15][C:16]1=[O:17])([O-:3])=[O:2]

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 225235-NitroindoleHCID 145742L-Proline

생성물 1

HCID 152282635-(5-Nitroindol-3-ylmethyl)-2,2-dimethyl-1,3-dioxane4,6-dione수율 81.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

An adaption of the procedure of Flaugh1 was used. Thus, a solution of 5-nitroindole (50.0 g, 0.31 mol), Meldrum's acid (46.0 g, 0.32 mol), 37% aqueous formaldehyde (26.0 mL, 0.32 mol) and proline (1.8 g, 0,016 mol) in 200 mL of acetonitrile was stirred at room temperature for 18 h. The resulting thick yellow slurry was filtered and the filtercake was washed with acetonitrile, then acetone and finally with ether. This material was dried in vacuo to give the title compound (80.0 g, 81%) as a bright yellow solid, m.p. 182° C. (dec). The mother liquor was concentrated and then diluted with H2O, and the resulting solid was collected and washed and dried as before. This gave a second crop of the product (7.0 g) as a darker yellow solid. Total yield=87.0 g (89%).

후처리

  1. filtrationThe resulting thick yellow slurry was filtered
  2. washthe filtercake was washed with acetonitrile
  3. customThis material was dried in vacuo

출처 및 근거

ORD 기록
ord-af33cdcee8c04c808c2bc21313a031c2
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05434154

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