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

HRID 53143

반응식

HRID 53143 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.[CH2:23]=O>C(#N)C.N1CCC[C@H]1C(O)=O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:23][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 3

HCID 712FormaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 225235-Nitroindole

생성물 1

HCID 152282635-(5-Nitroindol-3-ylmethyl)-2,2-dimethyl-1,3-dioxane4,6-dione수율 81%

시약·촉매·용매 2

HCID 145742L-Proline촉매HCID 6342Acetonitrile용매

실험 절차

An adaption of the procedure of Flaugh1 was used. Thus, a solution of 5-nitroindole (50.0 g, 0.32 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, mp 182° C. (dec). The mother liquor was concentrated and then diluted with H2O, and the resulting solid was collected, washed and dried as before to give a second crop of the product (7.0 g) as a darker yellow solid. Total yield=87.0 g (89%): IR (KBr) 3330, 1767, 1732 cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ11.64 (s, 1H), 8.63 (d, J=2.2 Hz, 1H), 7.96 (dd, J=9.0, 2.2 Hz, 1H), 7.49 (d, J=9.0 Hz, 1H), 7.33 (d, J=2.2 Hz, 1H), 4.84 (t, J=4.6 Hz, 1H), 3.45 (d, J=4.5 Hz, 2H), 1.78 (s, 3H), 1.55 (s, 3H). Anal. Calcd for C15H14N2O6 : C, 56.60; H, 4.43; N, 8.80. Found: C, 56.62; H, 4.41; N, 8.91.

후처리

  1. filtrationThe resulting thick yellow slurry was filtered
  2. washthe filtercake was washed with acetonitrile

출처 및 근거

ORD 기록
ord-ee9fddc37b7c426e95202c33d76ad144
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618816

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