Formaldehyde → 5-(4-Methyl-5-nitroindol-3-ylmethyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 441094ノート

反応式

HRID 441094 の反応式
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH3:14][C:15]1([CH3:23])[O:22][C:20](=[O:21])[CH2:19][C:17](=[O:18])[O:16]1.[CH2:24]=O>C(#N)C.N1CCCC1C(O)=O>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:24][CH:19]1[C:20](=[O:21])[O:22][C:15]([CH3:23])([CH3:14])[O:16][C:17]1=[O:18])=[CH:5][NH:6]2

参加物

6

反応物 3

HCID 712FormaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 154534624-methyl-5-nitro-1H-indole

生成物 1

HCID 224057085-(4-Methyl-5-nitroindol-3-ylmethyl)-2,2-dimethyl-1,3-dioxane-4,6-dione収率 64%

試薬・触媒・溶媒 2

HCID 614proline dl-form触媒HCID 6342Acetonitrile溶媒

実験手順

An adaption of the procedure of Flaugh was used. Thus, a solution of 4-methyl-5-nitroindole (0.880 g, 5.00 mmol), Meldrum's acid (0.864 g, 6.00 mmol), 37% aqueous formaldehyde (0.5 mL, 6.0 mmol) and D,L-proline (0.029 g, 0.25 mmol) in 25 mL of acetonitrile was stirred at room temperature for 72 h. The resulting yellow slurry was stored at -20° C. and then the cold mixture was filtered. The filtercake was washed with cold acetonitrile and ether, and then it was dried in vacuo to give the title compound (1.055 g, 64%) as a canary-yellow solid, mp 196°-198° C. (dec): IR (KBr) 3338, 1782, 1742 cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ 11.46 (br s, 1H), 7.61 (d, J=8.9 Hz, 1H), 7.32 (d, J=8.9 Hz, 1H), 7.25 (d, J= 2.4 Hz, 1H), 4.74 (t, J=5.0 Hz, 1H), 3.64 (d, J=4.9 Hz, 1H), 2.80 (s, 3H), 1.84 (s, 3H), 1.69 (s, 3H). Anal. Calcd for C16H16N2O6 : C, 57.83; H, 4.85; N, 8.43. Found: C, 57.42; H, 4.68; N, 8.52.

後処理

  1. customwas stored at -20° C.
  2. filtrationthe cold mixture was filtered
  3. washThe filtercake was washed with cold acetonitrile and ether
  4. customit was dried in vacuo

出典と根拠

ORDレコード
ord-fb25776e0c2548fc9d8ef5183d061b96
出典データセット
uspto-grants-1996_05
特許番号
US05521188

反応ノート

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