Sodium Bicarbonate → HCID 178468377, compound

HRID 1466592Notes

Reaction equation

HRID 1466592 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[O:13])[CH2:9][C:10](=[O:12])[CH3:11])[CH:5]=[CH:6][CH:7]=1.[N:14]([O-])=[O:15].[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[O:13])[C:9](=[N:14][OH:15])[C:10](=[O:12])[CH3:11])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 152569661-(3-Chlorophenyl)butane-1,3-dioneHCID 23668193Sodium Nitrite

Product 1

HCID 178468377HCID 178468377, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 1-(3-chlorophenyl)butane-1,3-dione (0.75 g, 3.8 mmol) in 15 mL acetic acid was slowly added sodium nitrite (0.560 g, 8.11 mmol) as a solution in 1.5 mL water. The reaction was stirred at 0° C. for 30 minutes and then warmed to room temperature. After an additional 4 hours, the reaction was poured into aqueous saturated sodium bicarbonate and extracted three times with dichloromethane. The combined extracts were dried over magnesium sulfate and concentrated to yield 765.7 mg (89%) of 1-(3-chlorophenyl)-2-(hydroxyimino)butane-1,3-dione, which was carried forward without further purification. LCMS (ESI) m+H=226; 1H NMR (400 MHz, DMSO-d6) δ: 7.81 (d, 1H), 7.80 (s, 1H), 7.75 (d, 1H), 7.62 (t, 1H), 2.60 (s, 1H), 2.48 (s, 3H).

Workup

  1. customTo a 0° C.
  2. temperaturewarmed to room temperature
  3. waitAfter an additional 4 hours
  4. extractionextracted three times with dichloromethane
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6e08fba9f1ea4862a4e12aa5ccc3bdce
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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