Water → (3-Bromo-2-nitro-phenylamino)-acetic acid ethyl ester

HRID 216725Notes

Reaction equation

HRID 216725 reaction equation
Cl.C([NH:4][CH2:5][C:6]([OH:8])=[O:7])C.[CH:9](N(C(C)C)CC)(C)[CH3:10].[Br:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21](F)[C:20]=1[N+:26]([O-:28])=[O:27].O>CC(N(C)C)=O>[CH2:9]([O:8][C:6](=[O:7])[CH2:5][NH:4][C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([Br:18])[C:20]=1[N+:26]([O-:28])=[O:27])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27831521-Bromo-3-fluoro-2-nitrobenzeneHCID 190114022-(Ethylamino)acetic acid hydrochloride

Product 1

HCID 59392671(3-Bromo-2-nitro-phenylamino)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

9.90 g (69.6 mmol) ethylglycinate hydrochloride are suspended under argon in 100 mL of dry DMA. 24.3 mL (139 mmol) diisopropylethylamine and 10.21 g (46.4 mmol) of 2-bromo-6-fluoronitrobenzene are then added at RT. The orange solution is then heated to 80° C. for 16 h. After cooling, the reaction mixture is poured onto iced-cold water and the suspension is collected by filtration to afford, after drying in HV at 50° C., the title compound as a dark orange solid, which is used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. filtrationthe suspension is collected by filtration
  3. customto afford
  4. customafter drying in HV at 50° C.
  5. customthe title compound as a dark orange solid, which is used in the next step without further purification

Sources & evidence

ORD record
ord-ff9c87478d5f4a5088211a355c2346b6
Source dataset
uspto-grants-2012_06
Patent number
US08193189B2

Reaction notes

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