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Hydrochloric Acid → 6-Benzyl-1-cyano-4-hydroxy-5-oxo-5,6-dihydro-[2,6]naphthyridine-3-carboxylic acid methyl ester

HRID 1410761
Notes
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Reaction equation

HRID 1410761 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7](I)[C:8]2[CH:9]=[CH:10][N:11]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12](=[O:16])[C:13]=2[C:14]=1[OH:15])=[O:4].[C:25]([Cu])#[N:26].[NH4+].[OH-].Cl>CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:25]#[N:26])[C:8]2[CH:9]=[CH:10][N:11]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12](=[O:16])[C:13]=2[C:14]=1[OH:15])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 867141156-Benzyl-4-hydroxy-1-iodo-5-oxo-5,6-dihydro-[2,6]naphthyridine-3-carboxylic acid methyl esterHCID 178418546HCID 178418546, compound

Product 1

HCID 682976046-Benzyl-1-cyano-4-hydroxy-5-oxo-5,6-dihydro-[2,6]naphthyridine-3-carboxylic acid methyl esterYield 58.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-benzyl-4-hydroxy-1-iodo-5-oxo-5,6-dihydro-[2,6]naphthyridine-3-carboxylic acid methyl ester (180 mg, 0.41 mmol) and CuCN (74 mg, 0.83 mmol) in 5 mL of DMF was refluxed for 8 min. The reaction mixture was cooled to r.t. and poured into a stirring mixture of 1% NH4OH solution and CH2Cl2. 4 M HCl was then added with vigorous stirring until no more solid was present. The aqueous layer was extracted with additional CH2Cl2, and the combined organic layer was dried over MgSO4 and concentrated. The crude was chromatographed (0-15% CH2Cl2/EtOAc+1% AcOH) to give 81 mg of the title compound as a pale yellow solid. MS: (−) m/z 334.00 (M−1).

Workup

  1. temperaturewas refluxed for 8 min
  2. extractionThe aqueous layer was extracted with additional CH2Cl2
  3. dry with materialthe combined organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude was chromatographed (0-15% CH2Cl2/EtOAc+1% AcOH)

Sources & evidence

ORD record
ord-f68fe35178d7422bb792609f46d6d8e3
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921389B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes