Dimethylamine → (3-Dimethylamino-4-nitrophenyl)acetic acid methyl ester

HRID 1864959Notes

Reaction equation

HRID 1864959 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7](Br)[CH:6]=1.[CH2:16]([N:18](CC)[CH2:19]C)C.CNC>O1CCCC1>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([N:18]([CH3:19])[CH3:16])[CH:6]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 23512304Methyl (3-bromo-4-nitrophenyl)acetate

Product 1

HCID 57683228(3-Dimethylamino-4-nitrophenyl)acetic acid methyl esterYield 52.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The (3-bromo-4-nitrophenyl)acetic acid methyl ester (0.320 g) obtained in Example 4 b) was dissolved in tetrahydrofuran (10 mL). To this solution were added triethylamine (0.237 g) and dimethylamine (2M tetrahydrofuran; 0.58 mL), and stirred overnight while heating. The reaction mixture was concentrated and purified by column chromatography on silica gel with ethyl acetate:hexane=1:4 to give the title compound (0.145 g) as an orange oil.

Workup

  1. temperaturewhile heating
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by column chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-972829bca93a40c5a6fdea4310c1af56
Source dataset
uspto-grants-2009_12
Patent number
US07625948B2

Reaction notes

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