Hydrochloric Acid → 4-Methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylic acid

HRID 1817343Notes

Reaction equation

HRID 1817343 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:11](=[O:13])[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH2:9][CH2:8][C:7]=2[C:6]([C:23]([O:25]CC)=[O:24])=[N:5][CH:4]=1.O.Cl>C1COCC1>[CH3:1][O:2][C:3]1[C:12]2[C:11](=[O:13])[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH2:9][CH2:8][C:7]=2[C:6]([C:23]([OH:25])=[O:24])=[N:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 67515740Ethyl 4-methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

Product 1

HCID 690648344-Methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate (15.2 g) in THF (150 mL) was added LiOH monohydrate (5.16 g) and sufficient water to dissolve the solids. The reaction was allowed to stir at room temperature for 1.5 hours. The reaction was neutralized with 125 mL of 1N HCl and the THF was removed in vacuo. The resulting slurry was partitioned between CHCl3 and 10% aqueous KHSO4. The combined organics were dried over sodium sulfate, filtered, and concentrated to dryness to afford the desired product as a pale tan foam. LRMS (M+1)=343.0

Workup

  1. dissolutionto dissolve the solids
  2. customthe THF was removed in vacuo
  3. customThe resulting slurry was partitioned between CHCl3 and 10% aqueous KHSO4
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-537cf59db69248ccaeef4705726953ec
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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