Water → (3-Dimethylamino-phenylamino)-acetic acid methyl ester

HRID 2115577Notes

Reaction equation

HRID 2115577 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.Br[CH2:12][C:13]([O:15][CH3:16])=[O:14].CCN(C(C)C)C(C)C.O>C1COCC1.C(OCC)(=O)C>[CH3:16][O:15][C:13](=[O:14])[CH2:12][NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([N:2]([CH3:10])[CH3:1])[CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 60984Methyl bromoacetateHCID 76084N,N-dimethyl-m-phenylenediamineHCID 81531Diisopropylethylamine

Product 1

HCID 66886120(3-Dimethylamino-phenylamino)-acetic acid methyl esterYield 70%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N,N-dimethyl-m-phenylenediamine (120 mmol) in THF (500 mL) was added methyl bromoacetate (132 mmol) and DIPEA (264 mmol). The reaction mixture was refluxed for 16 h. Water (200 mL) and ethyl acetate (300 mL) were added, the layers were separated and the aqueous layer was extracted with ethyl acetate (2×200 mL). The combined organic layers were washed with water (4×100 mL) and brine (100 mL) and dried over Na2SO4. The solvents were removed in vacuo and the residue was purified by flash-chromatography (ethyl acetate/heptane 1:4) to give 17.5 g (84.0 mmol, 70%) of an oily product which crystallized slowly.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×200 mL)
  4. washThe combined organic layers were washed with water (4×100 mL) and brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvents were removed in vacuo
  7. customthe residue was purified by flash-chromatography (ethyl acetate/heptane 1:4)

Sources & evidence

ORD record
ord-2dadb3bb76f543d7a35432973fadad9d
Source dataset
uspto-grants-2008_10
Patent number
US07435815B2

Reaction notes

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