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Hydrochloric Acid → 1-Benzyl-4-(benzyloxy)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylic acid

HRID 1179326
Notes
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Reaction equation

HRID 1179326 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:10]([C:26]([O:28]C)=[O:27])[C:9]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl>C1COCC1>[CH2:1]([N:8]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:10]([C:26]([OH:28])=[O:27])[C:9]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 58977987Methyl 1-benzyl-4-(benzyloxy)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 589780031-Benzyl-4-(benzyloxy)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 1-benzyl-4-(benzyloxy)-2-oxo-1,2-dihydro-1,5naphthyridine-3-carboxylate (0.65 g, 1.62 mmol) in THF (20 mL) was added sodium hydroxide (16.2 mL, 1 N) and the solution was heated to 80° C. and after 1.5 hours the reaction was completed. The reaction was allowed to cool and then the THF was removed leaving the product in water. The water was acidified with 1N HCl to adjust the pH to 3 and the resulting crude solids were collected by vacuum filtration and taken on as is.

Workup

  1. temperatureto cool
  2. customthe THF was removed
  3. customleaving the product in water
  4. filtrationthe resulting crude solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-1f1e445520c040b2a9fad9cf0e0ee5e8
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07279487B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes