Hydrazine hydrate (1:1) → 1-(6-Amino-5-methoxy-2,3-dihydro-1H-indol-1-yl)-2-(dimethylamino)ethan-1-one

HRID 1014247

反応式

HRID 1014247 の反応式
[CH3:1][N:2]([CH3:20])[CH2:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([N+:15]([O-])=O)[CH:13]=2)[CH2:8][CH2:7]1)=[O:5].O.NN>CO.[Fe](Cl)(Cl)Cl>[CH3:20][N:2]([CH2:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[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 594418292-(Dimethylamino)-1-(5-methoxy-6-nitroindolin-1-yl)ethanone

生成物 1

HCID 534147641-(6-Amino-5-methoxy-2,3-dihydro-1H-indol-1-yl)-2-(dimethylamino)ethan-1-one収率 69.5%

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-[5-(methyloxy)-6-nitro-2,3-dihydro-1 H-indol-1-yl]-2-oxoethanamine (26.6 g, 95 mmol), iron(III)chloride (3.09 g, 19.05 mmol), activated carbon (25 g, 95 mmol), and hydrazine hydrate (37.4 mL, 762 mmol) in methanol (500 mL) was warmed to 65° C. and maintained overnight. The reaction was filtered through celite while still warm and all methanol was removed under reduced pressure. The solids were partitioned between ethyl acetate (ca 1 L) and saturated sodium chloride (ca 1 L) and the aqueous layer was washed twice with ethyl acetate (ca 500 mL). The combined organic layers were dried over sodium sulfate, taken to a residue under reduced pressure, and the derived solids triturated with hexanes/diether ether and filtered to afford 1-[(dimethylamino)acetyl]-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine (16.46 g, 69.3% yield) as an off-white solid: NMR: 1H NMR (400 MHz, DMSO-d6) δ ppm 2.23 (s, 6 H), 2.95 (t, J=8.25 Hz, 2 H), 3.11 (s, 2H), 3.69 (s, 3 H), 4.07 (s, 2 H), 4.61 (s, 2 H), 6.68 (s, 1 H), 7.53 (s, 1 H).

後処理

  1. temperaturemaintained overnight
  2. filtrationThe reaction was filtered through celite
  3. temperaturewhile still warm
  4. customall methanol was removed under reduced pressure
  5. customThe solids were partitioned between ethyl acetate (ca 1 L) and saturated sodium chloride (ca 1 L)
  6. washthe aqueous layer was washed twice with ethyl acetate (ca 500 mL)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. customthe derived solids triturated with hexanes/diether ether
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-e52e6f4cd60c4ad8b27a9d5c6ddaf426
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

関連ノート

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