Sodium Glycinate → HCID 21189992, compound

HRID 1600728Notes

Reaction equation

HRID 1600728 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): δ 2.306 (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-bff3172b217544049b30c443bed62ff7
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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