Sodium Nitrite → HCID 118468362, compound

HRID 629393Notes

Reaction equation

HRID 629393 reaction equation
N[C:2]1[C:11]([CH3:12])=[C:10]([CH3:13])[C:9]([Br:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N([O-])=[O:16].[Na+]>S(=O)(=O)(O)O>[Br:14][C:9]1[C:10]([CH3:13])=[C:11]([CH3:12])[C:2]([OH:16])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 118468297HCID 118468297, compound

Product 1

HCID 118468362HCID 118468362, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
100 °C

Procedure

To an aqueous solution (160 mL) of methyl 2-amino-5-bromo-3,4-dimethylbenzoate (28.0 g) in 25% sulfuric acid was added dropwise an aqueous solution (80.0 mL) of sodium nitrite (11.2 g) over 50 min at the internal temperature of 2-3° C. under ice-cooling. Then, 5% aqueous sulfuric acid solution (1600 mL) was added dropwise thereto over 50 min at 0-15° C. The reaction mixture was stirred at 100° C. for 2 hr. The reaction mixture was allowed to be cooled to room temperature, and the precipitate was collected by filtration, and washed with water to give the title compound (25.7 g).

Workup

  1. temperaturecooling
  2. temperatureto be cooled to room temperature
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-ffea680369c8417c90f3b94789db572e
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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