Hydrazine hydrate (1:1) → 1-[(dimethylamino)acetyl]-2,3-dihydro-1H-indol-6-amine

HRID 1014288ノート

反応式

HRID 1014288 の反応式
[CH3:1][N:2]([CH3:18])[CH2:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-])=O)[CH:13]=2)[CH2:8][CH2:7]1)=[O:5].O.NN>[Fe](Cl)(Cl)Cl.CO>[CH3:18][N:2]([CH2:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:15])[CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:1]

参加物

5

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 59441863N,N-dimethyl-2-(6-nitro-2,3-dihydro-1H-indol-1-yl)-2-oxoethanamine

生成物 1

HCID 594419761-[(dimethylamino)acetyl]-2,3-dihydro-1H-indol-6-amine収率 80.2%

試薬・触媒・溶媒 2

HCID 24380Iron chloride (FeCl3)触媒HCID 887Methanol溶媒

反応条件

温度
65 °C

実験手順

A suspension of N,N-dimethyl-2-(6-nitro-2,3-dihydro-1 H-indol-1-yl)-2-oxoethanamine (13.6 g, 54.6 mmol), hydrazine hydrate (21.42 mL, 436 mmol), iron (III) chloride (1.768 g, 10.91 mmol), activated carbon (15 g), and methanol (100 mL) was maintained at 65° C. for 12 hours, cooled, and filtered through celite (rinsed with additional methanol). Filtrates were concentrated, redissolved in ethyl acetate, and washed twice with saturated aqueous sodium chloride and sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered, and concentrated to afford 1-[(dimethylamino)acetyl]-2,3-dihydro-1H-indol-6-amine (9.6 g, 80% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.44 (d, J=1.40 Hz, 1 H), 6.83 (d, J=8.03 Hz, 1 H), 6.20 (dd, J=7.93, 2.11 Hz, 1 H), 4.94 (s, 2 H), 4.06 (t, J=8.43 Hz, 2 H), 3.14 (s, 2 H), 2.91 (t, J=8.33 Hz, 2 H), 2.25 (s, 6 H).

後処理

  1. temperaturecooled
  2. filtrationfiltered through celite (rinsed with additional methanol)
  3. concentrationFiltrates were concentrated
  4. dissolutionredissolved in ethyl acetate
  5. washwashed twice with saturated aqueous sodium chloride and sodium bicarbonate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-19f2a426c684410faeb9f8c364f4bbc8
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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