Hydrochloric Acid → HCID 53246413, compound

HRID 1915523Notes

Reaction equation

HRID 1915523 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:31]([O-])=O)=[C:6]2[C:11]=1[NH:10][CH:9]=[C:8]([C:12]([NH:14][C:15]1[CH:20]=[C:19]([OH:21])[C:18]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:17][C:16]=1[C:26]([CH3:29])([CH3:28])[CH3:27])=[O:13])[C:7]2=[O:30].Cl>[Pd].CCOC(C)=O>[NH2:31][C:5]1[CH:4]=[CH:3][CH:2]=[C:11]2[C:6]=1[C:7](=[O:30])[C:8]([C:12]([NH:14][C:15]1[CH:20]=[C:19]([OH:21])[C:18]([C:22]([CH3:23])([CH3:24])[CH3:25])=[CH:17][C:16]=1[C:26]([CH3:29])([CH3:28])[CH3:27])=[O:13])=[CH:9][NH:10]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59410104HCID 59410104, compound

Product 1

HCID 53246413HCID 53246413, compoundYield 48.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A flask charged with 8-bromo-N-(2,4-di-tert-butyl-5-hydroxyphenyl)-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxamide (430 mg, 0.83 mmol)) and Pd/C (60 mg, 0.56 mmol) was evacuated under vacuum, followed by purging with N2. EtOAc (4 mL) and HCl (1 mL of 1 M, 1.000 mmol) were added followed by evacuating under vacuum. The reaction was stirred overnight under an atmosphere of hydrogen, filtered through a plug of celite and concentrated to get 5-amino-N-(2,4-ditert-butyl-5-hydroxy-phenyl)-4-oxo-1H-quinoline-3-carboxamide (164 mg, 48%). LC/MS: m/z 408.5 (M+H)+ at 1.98 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customwas evacuated under vacuum
  2. customby purging with N2
  3. customby evacuating under vacuum
  4. filtrationfiltered through a plug of celite
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-de30c896881343fc845b1f3384f1afd8
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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