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

HRID 441094노트

반응식

HRID 441094 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 614proline dl-form촉매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fb25776e0c2548fc9d8ef5183d061b96
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521188

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