1,4-Difluoro-2-methyl-5-nitrobenzene → HCID 21189988, compound

HRID 1600745Notes

Reaction equation

HRID 1600745 reaction equation
[F: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].[F: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 2306581,4-Difluoro-2-methyl-5-nitrobenzeneHCID 4684308Sodium Glycinate

Product 1

HCID 21189988HCID 21189988, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
28 °C

Procedure

To a stirred solution of 2,5-difluoro-4-nitrotoluene (0.550 g. 3.18 mmol) in DMF (5.0 mL) was added dropwise a solution of sodium glycinate (0.308 g, 3.18 mmol, Aldrich, used as received) in water (1.0 mL). The resulting suspension was stirred at 28° C. overnight. The solid was filtered and dried under vacuum to give 0.168 g (23%) of crude product. It was purified as follows. 0.150 g material was boiled in ethyl acetate (5.0 mL) and filtered while hot to give 0.134 g (18%) of the pure (1H NMR) title compound as a yellow powder. 1H NMR (DMSO-d6): 2.213 (s, 3H), 3.428 (d, 2H, J=3.9 Hz), 6.765 (d, 1H, J=6.9 Hz), 7.700 (d, 1H, J=10.5 Hz), 8.728 (s, 1H).

Workup

  1. filtrationThe solid was filtered
  2. customdried under vacuum
  3. customto give 0.168 g (23%) of crude product
  4. customIt was purified
  5. filtrationfiltered while hot

Sources & evidence

ORD record
ord-35d2445062a04560a263680e5330ca21
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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