Dimethylamine → N,N-dimethyl-2-(6-nitro-2,3-dihydro-1H-indol-1-yl)-2-oxoethanamine

HRID 1014287노트

반응식

HRID 1014287 반응식
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21](Cl)=[O:22].[CH3:24][NH:25][CH3:26].C1COCC1>ClCCl.C(=O)(O)[O-].[Na+].O>[CH3:24][N:25]([CH3:26])[CH2:20][C:21]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH2:8][CH2:9]1)=[O:22]

참가 물질

9

반응물 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 297576-NitroindolineHCID 89602Bromoacetyl chloride

생성물 1

HCID 59441863N,N-dimethyl-2-(6-nitro-2,3-dihydro-1H-indol-1-yl)-2-oxoethanamine수율 90%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

A suspension of 6-nitro-2,3-dihydro-1H-indole (10 g, 60.9 mmol) and potassium carbonate (16.84 g, 122 mmol) in dichloromethane (250 mL) was treated with bromoacetylchloride (6.33 mL, 76 mmol) and stirred for 25 minutes. Water was added and the organic layer was dried over sodium sulfate, filtered, taken to a residue under reduced pressure. The residue was redissolved in THF and 2.0M dimethyl amine in THF (Aldrich, 152 mL, 305 mmol) was added. The solution was stirred overnight, diluted with saturated sodium bicarbonate, and the organic layer was dried over sodium sulfate, filtered, taken to a residue under reduced pressure, and purified by column chromatography to afford N,N-dimethyl-2-(6-nitro-2,3-dihydro-1H-indol-1-yl)-2-oxoethanamine (13.6 g, 54.6 mmol, 90% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.80 (d, J=2.01 Hz, 1 H), 7.90 (dd, J=8.23, 2.21 Hz, 1 H), 7.48 (d, J=8.23 Hz, 1 H), 4.26 (t, J=8.53 Hz 2 H), 3.18-3.31 (m, 4 H), 2.28 (s, 6 H).

후처리

  1. dry with materialthe organic layer was dried over sodium sulfate
  2. filtrationfiltered
  3. dissolutionThe residue was redissolved in THF
  4. stirringThe solution was stirred overnight
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-9cd68f4f696e40018139e2736b343c14
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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