Sodium Glycinate → HCID 21189992, compound

HRID 1781020Notes

Reaction equation

HRID 1781020 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5](F)=[CH:4][C:3]=1[CH3:12].[NH2:13][CH2:14][C:15]([O-:17])=[O:16].[Na+:18]>CN(C=O)C.O>[Na+:18].[Br:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([NH:13][CH2:14][C:15]([O-:17])=[O:16])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 2

HCID 4684308Sodium GlycinateHCID 100369831-Bromo-4-fluoro-2-methyl-5-nitrobenzene

Product 1

HCID 21189992HCID 21189992, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 2-bromo-5-fluoro-4-nitrotoluene (1.662 g, 7.102 mmol, as prepared above) in DMF (7.0 mL) at 70° C., was added, dropwise, a solution of sodium glycinate (0.690 g, 7.11 mmol, Aldrich, used as received) in water (7.0 mL). The resulting suspension was stirred overnight at 70° C. The suspension was cooled to room temperature and the red solid was filtered, washed with acetone, and dried under vacuum to give 0.932 g (45%) of the pure (1H NMR) title compound as a red powder; 1H NMR (DMSO-d6): δ2.306 (s, 3H), 3.452 (d, 2H, J=3.9 Hz), 6.874 (s, 1H), 8.125 (s, 1H), 8.779 (s, 1H).

Workup

  1. temperatureThe suspension was cooled to room temperature
  2. filtrationthe red solid was filtered
  3. washwashed with acetone
  4. customdried under vacuum

Sources & evidence

ORD record
ord-1be67ca729984837a23c9cd02623e794
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

Loading…