Tetrahydrofuran → 1-(Methoxymethyl)-2-(1,3-thiazol-2-yl)-1H-indole-7-amine

HRID 1851370ノート

反応式

HRID 1851370 の反応式
[CH3:1][O:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N+:13]([O-])=O)[CH:6]=[C:5]1[C:16]1[S:17][CH:18]=[CH:19][N:20]=1.O1CCCC1.O.NN>O.O.O.O.O.O.[Fe](Cl)(Cl)Cl.CO>[CH3:1][O:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH2:13])[CH:6]=[C:5]1[C:16]1[S:17][CH:18]=[CH:19][N:20]=1

参加物

6

反応物 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 579018301-(Methoxymethyl)-7-nitro-2-(1,3-thiazol-2-yl)-1H-indole

生成物 1

HCID 579017321-(Methoxymethyl)-2-(1,3-thiazol-2-yl)-1H-indole-7-amine収率 97.5%

試薬・触媒・溶媒 2

HCID 16211236Trichloroiron;hexahydrate触媒HCID 887Methanol溶媒

実験手順

A mixture of 1-(methoxymethyl)-7-nitro-2-(1,3-thiazol-2-yl)-1H-indole (2.14 g), iron(III) chloride hexahydrate (0.12 g), activated carbon (1.20 g), tetrahydrofuran (10 mL) and methanol (10 mL) was heated under reflux for 20 min. To the reaction mixture was added hydrazine monohydrate (2.20 g) over 15 min while heating under reflux. The reaction mixture was heated under reflux for 2 hr, filtrated, and the filtrate was concentrated. The residue was dissolved in ethyl acetate, washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography and the title compound (1.87 g, yield 97%) was obtained as a yellow oil from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 20 min
  3. temperaturewhile heating
  4. temperatureunder reflux
  5. temperatureThe reaction mixture was heated
  6. temperatureunder reflux for 2 hr
  7. filtrationfiltrated
  8. concentrationthe filtrate was concentrated
  9. dissolutionThe residue was dissolved in ethyl acetate
  10. washwashed with saturated brine
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated

出典と根拠

ORDレコード
ord-74d40bdc0da041a1aedc65aa07ebaecf
出典データセット
uspto-grants-2015_02
特許番号
US08957070B2

反応ノート

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