1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-Chloro-2-(N-methoxy-N-methylamino)carbonyl-3-nitroindole

HRID 379822Notes

Reaction equation

HRID 379822 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N+:14]([O-:16])=[O:15])=[C:7]([C:11]([OH:13])=O)[NH:8]2)=[CH:4][CH:3]=1.Cl.[CH3:18][NH:19][O:20][CH3:21].CCN=C=NCCCN(C)C>CN(C=O)C.C(OCC)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N+:14]([O-:16])=[O:15])=[C:7]([C:11]([N:19]([O:20][CH3:21])[CH3:18])=[O:13])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 18367950HCID 18367950, compound

Product 1

HCID 183681976-Chloro-2-(N-methoxy-N-methylamino)carbonyl-3-nitroindoleYield 56%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 6-chloro-3-nitroindole-2-carboxylic acid (step 1, 2.35 g, 9.77 mmol) and N,O-dimethylhydroxylamine hydrochloride (3.81 g, 39.1 mmol) in DMF (50 ml) was added dropwise a dimethylformamide (15 ml) solution of WSC (5.61 g, 29.3 mmol) over 10 min. After stirring for 4 h the mixture was diluted with diethyl ether (200 ml) and washed with water (100 ml×4). The organic extract was dried (MgSO4) and solvent removed by evaporation. The crude product was recystallized from ethyl acetate to afford 1.55 g (56%) of the title compound.

Workup

  1. washwashed with water (100 ml×4)
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4) and solvent
  4. customremoved by evaporation

Sources & evidence

ORD record
ord-d44486feefd3462c9b94456e6d6ed477
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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