Sodium Glycinate → n-(5'-Chloro-4'-methyl-2'-nitrophenyl)glycine sodium salt

HRID 1781004Notes

Reaction equation

HRID 1781004 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[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].[Cl:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:13][CH2:14][C:15]([O-:17])=[O:16])[CH:7]=1

Participants

5

Reactant 2

HCID 4684308Sodium GlycinateHCID 101039792-Chloro-4-fluoro-5-nitrotoluene

Product 1

HCID 21190047n-(5'-Chloro-4'-methyl-2'-nitrophenyl)glycine sodium salt

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 2-chloro-4-fluoro-5-nitrotoluene (2.080 g, 10.97 mmol, as prepared above) in DMF (11.0 mL) at 70° C., was added dropwise, a solution of sodium glycinate (1.065 g, 10.97 mmol, Aldrich, used as received) in water (11.0 mL). The resulting suspension was stirred overnight at 70° C., cooled to room temperature, and the resulting red solid was filtered, washed with acetone (35 mL), and dried under vacuum to give 1.005 g (37%) of the pure (1H NMR) title compound as a red powder; 1H NMR (DMSO-d6): δ2.184 (s, 3H), 3.396 (d, 2H, J=4.2 Hz), 6.852 (s, 1H), 7.991 (s, 1H), 8.671 (s, 1H).

Workup

  1. temperaturecooled to room temperature
  2. filtrationthe resulting red solid was filtered
  3. washwashed with acetone (35 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ad3a05284c3544a09486d2295e29d42a
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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