Hydrochloric Acid → 3-Hydroxy-4-(2-isopropylphenyl)-6-methyl-1-carboxymethyl-2-pridinone

HRID 398379Notes

Reaction equation

HRID 398379 reaction equation
C([O:4][C:5]1[C:6](=[O:27])[N:7]([CH2:21][C:22]([O:24]CC)=[O:23])[C:8]([CH3:20])=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:17]([CH3:19])[CH3:18])(=O)C.[OH-].[Na+].Cl>C(O)C>[OH:4][C:5]1[C:6](=[O:27])[N:7]([CH2:21][C:22]([OH:24])=[O:23])[C:8]([CH3:20])=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:17]([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 230001763-Acetoxy-4-(2-isopropylphenyl)-6-methyl-1-ethoxycarbonylmethyl-2-pyridinone

Product 1

HCID 230002443-Hydroxy-4-(2-isopropylphenyl)-6-methyl-1-carboxymethyl-2-pridinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 3-acetoxy-4-(2-isopropylphenyl)-6-methyl-1-ethoxycarbonylmethyl-2-pyridinone from step 4 above (0.325 g, 0.95 mmol) in ethanol (4 mL) was added aqueous NaOH (2.2 mL of a 1.0 N solution, 2.2 mmol). The resulting solution was stirred at ambient temperature for 18 h. The solution was acidified with aqueous HCl (2.2 mL of a 1.0 N solution, 2.2 mmol) and the solvents were removed in vacuo to give the title compound as an amorphous solid containing NaCl (HPLC RT=18.67 min, method B).

Workup

  1. customwere removed in vacuo

Sources & evidence

ORD record
ord-f41ecff52916431084e8aa1fd0726d33
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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