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

HRID 1014287ノート

反応式

HRID 1014287 の反応式
[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]

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9cd68f4f696e40018139e2736b343c14
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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