Dimethylamine → HCID 10400418, compound

HRID 1887708Notes

Reaction equation

HRID 1887708 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[C:13]1(=O)[NH:17][C:16](=O)C2=CC=CC=C12.[C:24](Cl)(=[O:28])[C:25](Cl)=[O:26].CNC.C1COCC1>CCOCC>[CH3:16][N:17]([CH3:13])[C:24](=[O:28])[C:25]([C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9][CH:8]=1)=[O:26]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 6809PhthalimideHCID 8028TetrahydrofuranHCID 225235-NitroindoleHCID 65578Oxalyl chloride

Product 1

HCID 10400418HCID 10400418, compoundYield 147.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of 5-nitroindole (5.00 g, 30.8 mmol) and phtalimide (2.00 g, 40% by weight) in anhydrous ether (125 mL) was added oxalyl chloride (8.09 mL, 95.6 mmol). The resulting mixture was stirred at room temperature for 24 h. The solids were filtered off, rinsed with several portions of ether and air-dried for 15 min. This intermediate was suspended in 100 mL anhydrous ether and cooled to 0° C. To this mixture was 2M dimethylamine in THF (154 mL, 0.308 mol) added in small increments. After the addition was complete the reaction was stirred for an additional 1 h at room temperature. The volatiles were evaporated and the crude re-crystallized in refluxing MeOH afforded N,N-dimethyl-2-(5-nitro-1H-indol-3-yl)-2-oxoacetamide (5.2 g, 20.02 mmol, 65%).

Workup

  1. filtrationThe solids were filtered off
  2. washrinsed with several portions of ether
  3. customair-dried for 15 min
  4. temperaturecooled to 0° C
  5. additionadded in small increments
  6. additionAfter the addition
  7. stirringwas stirred for an additional 1 h at room temperature
  8. customThe volatiles were evaporated
  9. customthe crude re-crystallized
  10. temperaturein refluxing MeOH

Sources & evidence

ORD record
ord-be18ad2e2c1d45639b0933c1314cd304
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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