Hydrochloric Acid → HCID 14010769, compound

HRID 255674Notes

Reaction equation

HRID 255674 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20]([CH:21]=[O:22])=[CH:19][C:18](=[O:23])[C:13]([C:14]([O:16]C)=[O:15])=[CH:12]2)=[C:7]([CH3:24])[CH:6]=1)(=O)C.Cl.C(=O)([O-])O.[Na+].[Cl-].[Na+]>C(#N)C>[CH:21]([C:20]1[N:11]([C:8]2[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][C:7]=2[CH3:24])[CH:12]=[C:13]([C:18](=[O:23])[CH:19]=1)[C:14]([OH:16])=[O:15])=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 14010755HCID 14010755, compound

Product 1

HCID 14010769HCID 14010769, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 0.95 g of methyl 1-(4-acetoxy-2-methylphenyl)-6-formyl-4-oxo-1,4-dihydronicotinate was added 5 ml of 6N hydrochloric acid, and they were reacted at 100° C. for one hour. The reaction mixture was cooled to room temperature, and adjusted to a pH of 7.5 with a saturated aqueous sodium hydrogencarbonate solution. Then, 100 ml of acetonitrile was added, and the aqueous layer was saturated with sodium chloride. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride and then dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 0.6 g of 6-formyl-1-(4-hydroxy-2-methylphenyl)-4-oxo-1,4-dihydronicotinic acid having a melting point of 230°-250° C.

Workup

  1. customwere reacted at 100° C. for one hour
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-985f4584075d45a4bf2606e943c67c5f
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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