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

HRID 1014247

반응식

HRID 1014247 반응식
[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]

참가 물질

5

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 594418292-(Dimethylamino)-1-(5-methoxy-6-nitroindolin-1-yl)ethanone

생성물 1

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

시약·촉매·용매 2

HCID 24380Iron chloride (FeCl3)촉매HCID 887Methanol용매

반응 조건

온도
65 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e52e6f4cd60c4ad8b27a9d5c6ddaf426
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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