Hydrochloric Acid → 2-[(5-Bromo-2-nitrophenyl)(methyl)amino]acetic acid

HRID 1007103Notes

Reaction equation

HRID 1007103 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.[NH:12]([CH2:14][C:15]([OH:17])=[O:16])[CH3:13].C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N:12]([CH2:14][C:15]([OH:17])=[O:16])[CH3:13])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1088SarcosineHCID 11430Potassium CarbonateHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 226677282-[(5-Bromo-2-nitrophenyl)(methyl)amino]acetic acidYield 87%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 4-bromo-2-fluoro-1-nitro-benzene (9 g, 40 mmol), sarcosine (3.6 g, 40 mmol), and potassium carbonate (5.5 g, 40 mmol) in ethanol (100 ml) and water (40 ml) was heated to reflux for 5 hours. After cooling to room temperature, the mixture was diluted with water and was adjusted to pH 6 with 1N aqueous HCl solution. The yellow precipitate was collected, washed with water and dried in vacuo to obtain crude [(5-bromo-2-nitro-phenyl)-methyl-amino]-acetic acid (10 g, 87%). A portion of the crude sample was recrystallized from EtOAc/hexane to afford the pure [(5-bromo-2-nitro-phenyl)-methyl-amino]-acetic acid: mp 152-155° C.; 1H-NMR (DMSO-d6) δ 2.81 (s, 3H), 4.00 (s, 2H), 7.06 (dd, 1H, J=8.79, 1.98 Hz), 7.22 (d, 1H, J=1.98 Hz), 7.69 (d, 1H, J=8.79 Hz), 12.8 (s, 1H); MS (+APCI) m/z 289/291 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. customThe yellow precipitate was collected
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-dcc8de4f427148f981c7e11433672fc3
Source dataset
uspto-grants-2004_09
Patent number
US06794373B2

Reaction notes

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