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

HRID 441073

反応式

HRID 441073 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 145742L-Proline触媒HCID 6342Acetonitrile溶媒

実験手順

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) δ 11.64 (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.

後処理

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

出典と根拠

ORDレコード
ord-c3abbb39556548a69fc712b7ad612be1
出典データセット
uspto-grants-1996_05
特許番号
US05521188

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