Water → 1-(4-Benzamidophenylamino)-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridine-8-carboxylic acid

HRID 1029226Notes

Reaction equation

HRID 1029226 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[CH:26]=[CH:25][N:24]=[C:23]3[C:18]=2[C:19]2[CH:31]=[CH:30][C:29]([C:32]([O:34]C)=[O:33])=[CH:28][C:20]=2[C:21](=[O:27])[NH:22]3)=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].O>C1COCC1>[C:1]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]2[CH:26]=[CH:25][N:24]=[C:23]3[C:18]=2[C:19]2[CH:31]=[CH:30][C:29]([C:32]([OH:34])=[O:33])=[CH:28][C:20]=2[C:21](=[O:27])[NH:22]3)=[CH:14][CH:15]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 44205292Methyl 1-(4-benzamidophenylamino)-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridine-8-carboxylate

Product 1

HCID 442055041-(4-Benzamidophenylamino)-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridine-8-carboxylic acidYield 56.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

267 (220 mg, 0.47 mmol) and LiOH (56 mg, 2.37 mmol) were suspended in THF (2 mL) and H2O (2 mL) and stirred overnight at room temperature. The THF was removed, the mixture was diluted with H2O, and acidified to pH=5 with 1M HCl. The crude product was purified via HP-LC to provide 268 (120 mg, 56% yield) as a white solid. LC-MS (M+H=451, obsd.=451).

Workup

  1. customThe THF was removed
  2. additionthe mixture was diluted with H2O
  3. customThe crude product was purified via HP-LC

Sources & evidence

ORD record
ord-f0597d8d52924da295458d42e70917b3
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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