Dichloromethane → Methyl 6-(benzyl(2-ethoxy-2-oxoethyl)amino)-5-nitronicotinate

HRID 69647Notes

Reaction equation

HRID 69647 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[CH2:15]([NH:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl[CH2:29]Cl>>[CH2:15]([N:22]([CH2:23][C:24]([O:26][CH2:27][CH3:29])=[O:25])[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 346961Methyl 6-chloro-5-nitronicotinateHCID 422659Methyl 2-(benzylamino)acetate

Product 1

HCID 59416801Methyl 6-(benzyl(2-ethoxy-2-oxoethyl)amino)-5-nitronicotinateYield 90%

Procedure

Methyl 6-chloro-5-nitronicotinate (2.0 g, 9.23 mmol) was added to methyl 2-(benzylamino)acetate (6.0 g, 31.05 mmol) neat while stirring at room temperature. The viscous yellow reaction was heated to 90° C. for one h and then allowed to cool back to room temperature. The reaction was diluted with dichloromethane (20 mL) and purified via column chromatography (220 g SiO2, 20-30% gradient, ethyl acetate in hexanes) to yield the title compound (3.10 g, 90% yield) as a yellow oil. [M+H] calc'd for C18H19N3O6, 374; found, 374.

Workup

  1. customThe viscous yellow reaction
  2. temperaturewas heated to 90° C. for one h
  3. temperatureto cool back to room temperature
  4. custompurified via column chromatography (220 g SiO2, 20-30% gradient, ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2613ec8a73d14bd49b90c1a29171ad87
Source dataset
uspto-grants-2014_09
Patent number
US08822470B2

Reaction notes

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