Sodium Chloride → HCID 86692166, compound

HRID 1500175Notes

Reaction equation

HRID 1500175 reaction equation
[CH2:1]([O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)[CH3:2].[N:11]([O-])=O.[Na+].[CH2:15]([O:17][C:18](=[O:24])[CH2:19][C:20](=[O:23])[CH2:21][Cl:22])[CH3:16].[Na+].[Cl-].CC([O-])=O.[Na+]>C(O)(=O)C.OS(O)(=O)=O.O>[CH2:15]([O:17][C:18](=[O:24])[CH:19]([N:11]=[N:8][C:7]1[CH:9]=[CH:10][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=1)[C:20](=[O:23])[CH2:21][Cl:22])[CH3:16]

Participants

9

Reactant 5

HCID 5234Sodium ChlorideHCID 90764-EthoxyanilineHCID 69484Ethyl 4-chloroacetoacetateHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 86692166HCID 86692166, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
10 °C

Procedure

A 10 mL one-neck round-bottom flask was charged with 250.0 mg (0.24 mL, 1.825 mmol, 1.04 eq) 4-ethoxyaniline which was dissolved in 3.1 mL acetic acid at 10° C. (ice bath). To this cooled solution 128.0 mg (1.861 mmol, 1.06 eq) NaNO2 in 0.5 mL conc. H2SO4 were added and the reaction mixture was stirred at 10° C. for 1 h. In a second 25 ml one-neck round-bottom flask 288.6 mg (0.24 mL, 1.755 mmol, 1.0 eq) ethyl-4-chloro-3-oxobutanoate were dissolved in a mixture of 1.3 mL acetic acid and 2.6 mL water and cooled to 0° C. (ice bath+NaCl). After one hour stirring at 10° C. the generated solution of the diazonium salt was given to the second solution at 0° C. and stirred for further 15 min at this temperature. An aqueous solution of 1.58 g (19.305 mmol, 11 eq) NaOAc in 3.0 mL water was added to the reaction mixture at 0° C. and the product precipitated. Stirring at rt over night, filtration, washing with a small amount of water and drying under high pressure yielded the crude product which was used in the next reaction step without further purification.

Workup

  1. customwas given to the second solution at 0° C.
  2. stirringstirred for further 15 min at this temperature
  3. customthe product precipitated
  4. stirringStirring at rt over night
  5. filtrationfiltration
  6. washwashing with a small amount of water
  7. customdrying under high pressure

Sources & evidence

ORD record
ord-0c5bb74a53a34dea85cd7c7cbe809532
Source dataset
uspto-grants-2015_12
Patent number
US09206115B2

Reaction notes

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