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

HRID 1014287Notes

Reaction equation

HRID 1014287 reaction equation
[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]

Participants

9

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-9cd68f4f696e40018139e2736b343c14
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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