Sulfuric Acid → HCID 21907510, compound

HRID 1247455Notes

Reaction equation

HRID 1247455 reaction equation
N[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:12])[C:5]([Br:13])=[CH:4][CH:3]=1.N([O-])=[O:15].[Na+].OS(O)(=O)=O>O>[Br:13][C:5]1[C:6]([CH3:12])=[C:7]([C:2]([OH:15])=[CH:3][CH:4]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21907549Methyl 6-amino-3-bromo-2-methylbenzoateHCID 23668193Sodium Nitrite

Product 1

HCID 21907510HCID 21907510, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

A 0° C. suspension of Example 106A (1 g, 4.1 mmol) in water (6 mL) was treated dropwise with a solution of NaNO2 (285 mg) in water (1.25 mL), stirred at 0° C. for 15 minutes, then added slowly to a 90° C. solution of concentrated H2SO4 (4 mL) in water (4 mL). The reaction was stirred at 90° C. for 45 minutes, cooled to room temperature, and extracted three times with diethyl ether. The combined extracts were washed with aqueous NaHCO3 and brine, dried (MgSO4), filtered, and concentrated to give 0.87 g of the desired product. MS (ESI(−)) m/e 226 (M−H)−.

Workup

  1. stirringThe reaction was stirred at 90° C. for 45 minutes
  2. temperaturecooled to room temperature
  3. extractionextracted three times with diethyl ether
  4. washThe combined extracts were washed with aqueous NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1d6fc0828fe34583b04d0a2bd786395c
Source dataset
uspto-grants-2006_10
Patent number
US07129260B2

Reaction notes

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