Sulfuric Acid → HCID 21266437, compound

HRID 566722Notes

Reaction equation

HRID 566722 reaction equation
O[C:2]1([C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[CH2:7][NH:6][C:5](=[O:8])[CH:4]=[C:3]1[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1.OS(O)(=O)=O>C(Cl)(Cl)Cl>[C:17]1([CH3:21])[CH:18]=[CH:19][CH:20]=[C:15]([C:2]2[C:3]([C:9]3[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=3)=[CH:4][C:5](=[O:8])[NH:6][CH:7]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 21266518HCID 21266518, compound

Product 1

HCID 21266437HCID 21266437, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 5-hydroxy-5-m-tolyl-5,6-dihydro-1H-[4,4′]bipyridinyl-2-one (280 mg, 1.0 mmole) in CHCl3 (5 mL) at r.t. was added 1 ml of conc. H2SO4. The resulting mixture was heated to 55° C. for 1 hr. The mixture was cooled down to r.t. and was carefully quenched with aqueous sodium carbonate. Standard work up (extraction of compound with methylene chloride), followed by purification (silica gel, methanol/methylene chloride) gave the title compound. MS (m/z): Calcd. C17H14N2O(M+): 262, found (M+H)+: 263.3.

Workup

  1. temperatureThe mixture was cooled down to r.t.
  2. customwas carefully quenched with aqueous sodium carbonate
  3. extractionStandard work up (extraction of compound with methylene chloride)
  4. customfollowed by purification (silica gel, methanol/methylene chloride)

Sources & evidence

ORD record
ord-9a52c5726cbb4f75ade4cf7857ce4f9d
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

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