Sulfuric Acid → HCID 131719371, compound

HRID 1378920Notes

Reaction equation

HRID 1378920 reaction equation
C(OC(=O)[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[CH:11]1[CH:16]=[CH:15][CH2:14][N:13](C(OCC)=O)[N:12]1[C:22]([O:24]CC)=O)C.OS(O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>O>[NH:13]1[CH2:14][CH2:15][CH:16]=[C:11]2[C:6]3[N:7]=[CH:8][CH:9]=[CH:10][C:5]=3[C:22](=[O:24])[N:12]12

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 53698348HCID 53698348, compound

Product 1

HCID 131719371HCID 131719371, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

6.6 g of 2-(1,2-diethoxycarbonyl-1,2,3,6-tetrahydropyridazin-3-yl)nicotinic acid ethyl ester are mixed with 15 ml water and 60 ml of H2SO4 added with cooling. The reaction mixture is heated under nitrogen to 120° over 1 hr in a hot oil bath. The mixture is slowly poured into 125 g Na2CO3 and 250 g of ice and 125 ml of water. The alkaline mixture is filtered through celite and repeatedly extracted with ethylacetate (8×100 ml) and the extracts dried over MgSO4. After filtration the solvent is removed by evaporation under vacuum to yield the title compound which is recrystalized from CH3CN.

Workup

  1. additionadded
  2. temperaturewith cooling
  3. temperatureThe reaction mixture is heated under nitrogen to 120° over 1 hr in a hot oil bath
  4. filtrationThe alkaline mixture is filtered through celite
  5. extractionrepeatedly extracted with ethylacetate (8×100 ml)
  6. dry with materialthe extracts dried over MgSO4
  7. filtrationAfter filtration the solvent
  8. customis removed by evaporation under vacuum

Sources & evidence

ORD record
ord-1ff5aa96347d46ff849dc5ef443eeecf
Source dataset
uspto-grants-1997_09
Patent number
US05670456

Reaction notes

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