Water → [(5-Bromo-2-nitro-phenyl)-n-butyl-amino]acetic acid

HRID 1007104Notes

Reaction equation

HRID 1007104 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[CH2:12]([NH:16][CH2:17][C:18]([OH:20])=[O:19])[CH2:13][CH2:14][CH3:15].O>C(O)C.[OH-].[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N:16]([CH2:17][C:18]([OH:20])=[O:19])[CH2:12][CH2:13][CH2:14][CH3:15])[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 413376NoName_600HCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 22667732[(5-Bromo-2-nitro-phenyl)-n-butyl-amino]acetic acidYield 22.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 4-bromo-2-fluoro-nitro benzene (34 g, 0.15 mol), N-n-butyl glycine (20 g, 0.15 mol) in ethanol (600 ml), and water (150 ml) was heated to reflux for 6 hours. After cooling to room temperature, the mixture was diluted with 2N sodium hydroxide, extracted with CH2Cl2 and the pH was adjusted to 5 with 1N HCl. The mixture was extracted with CH2Cl2, the CH2Cl2 solution was dried (MgSO4) and evaporated to obtain the crude product (11 g, 22%) as a brown oil, which was used without further purification. 1H-NMR (DMSO-d6) δ 0.84 (t, J=7.30 Hz, 3H), 1.23 (m, 2H), 1.45 (m, 2H), 3.18 (t, J=7.30 Hz, 2H), 3.91 (s, 2H), 7.16 (dd, J=8.68, 1.91 Hz, 1H), 7.40 (d, J=1.94 Hz, 1H), 7.69 (d, J=8.68 Hz, 1H); MS (EI) m/z 331 (M+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 hours
  3. extractionextracted with CH2Cl2
  4. extractionThe mixture was extracted with CH2Cl2
  5. dry with materialthe CH2Cl2 solution was dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-50f8eb7a202c437796f9e0f6e4015fc2
Source dataset
uspto-grants-2004_09
Patent number
US06794373B2

Reaction notes

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