Hydrochloric Acid → HCID 67264300, compound

HRID 1688024Notes

Reaction equation

HRID 1688024 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:12]([CH3:14])[CH3:13])[CH:5]=[C:6](F)[C:7]=1[N+:8]([O-:10])=[O:9].[OH-].[Na+].CS(C)=[O:19].Cl>O>[CH3:13][N:12]([CH3:14])[C:4]1[CH:3]=[C:2]([F:1])[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([OH:19])[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl Sulfoxide2×HCID 14798Sodium HydroxideHCID 672643313,5-Difluoro-N,N-dimethyl-4-nitrobenzenamine

Product 1

HCID 67264300HCID 67264300, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

(3,5-Difluoro-4-nitro-phenyl)-dimethyl-amine (0.630 g, 3.12 mmol) and 19.1 M of Sodium hydroxide in Water (0.400 mL) in Water (4 mL) and Dimethyl sulfoxide (8 mL) was heated to 70° C. Additional DMSO (8 mL) was added to solubilize the mixture. After 2 h, the solution was cooled then rendered acidic with 12.0 M of Hydrogen Chloride in Water (0.80 mL). The yellow precipitate was collected, using water to aid in the transfer and to rinse the solids. 5-Dimethylamino-3-fluoro-2-nitro-phenol was isolated as yellow solids (598 mg, 96%). 1H-NMR (DMSO): 11.10 (s, 1H), 6.29 (d, 1H, J=15.6 Hz), 6.02 (s, 1H), 3.01 (s, 6H); 19F−NMR (DMSO): −118.

Workup

  1. temperaturethe solution was cooled
  2. customThe yellow precipitate was collected
  3. washto rinse the solids

Sources & evidence

ORD record
ord-482814faa897403a847a3804f81fab6e
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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