2-Aminophenol → HCID 58168040, compound

HRID 1029115Notes

Reaction equation

HRID 1029115 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.[NH2:17][C:18]1[CH:23]=C[CH:21]=[CH:20][C:19]=1O.[C:25](=[O:28])([O-])[O-].[K+].[K+]>CN(C=O)C.CO>[NH2:17][C:18]1[CH:23]=[C:25]([CH:21]=[CH:20][CH:19]=1)[O:28][C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2

Participants

6

Reactant 3

HCID 58012-AminophenolHCID 11430Potassium CarbonateHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Product 1

HCID 58168040HCID 58168040, compoundYield 12.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (30 mg, 0.13 mmol), 2-aminophenol (43 mg, 0.39 mmol), and potassium carbonate (90 mg, 0.65 mmol) were suspended in DMF (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, and filtered through a membrane. The crude product was purified via prep-LC-MS to provide 133 (5 mg, 12% yield) as a solid. LC-MS (M+H=304, obsd.=304). 1H NMR (400 MHz, d6-DMSO): δ 11.72 (s, 1H), 9.68 (s, 2H), 8.88 (d, 1H), 8.35 (d, 1H), 8.18 (m, 1H), 8.01 (d, 1H), 7.76 (t, 1H), 7.58 (t, 1H), 7.02 (m, 2H), 6.78 (t, 1H), 6.48 (d, 1H).

Workup

  1. filtrationfiltered through a membrane
  2. customThe crude product was purified via prep-LC-MS

Sources & evidence

ORD record
ord-4c8bf03fc64245dcad10d27cd75672e9
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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