Formaldehyde → HCID 53247630, compound

HRID 1915524Notes

Reaction equation

HRID 1915524 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:30])[C:5]([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])=[CH:6][NH:7]2.[CH2:31]=O>[Pd]>[C:26]([C:16]1[CH:17]=[C:18]([C:22]([CH3:23])([CH3:24])[CH3:25])[C:19]([OH:21])=[CH:20][C:15]=1[NH:14][C:12]([C:5]1[C:4](=[O:30])[C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[NH:1][CH3:31])[NH:7][CH:6]=1)=[O:13])([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 53246413HCID 53246413, compound

Product 1

HCID 53247630HCID 53247630, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A flask charged with 5-amino-N-(2,4-ditert-butyl-5-hydroxy-phenyl)-4-oxo-1H-quinoline-3-carboxamide (23 mg, 0.06 mmol), Pd/C (5 mg, 0.05 mmol) and formaldehyde (5 μL of 38% w/v, 0.06 mmol) was evacuated under vacuum, followed by purging with N2. Methanol (1 mL) was added followed by evacuating under vacuum. The reaction mixture was stirred overnight under an atmosphere of hydrogen, filtered through a plug of celite and concentrated to get N-(2,4-ditert-butyl-5-hydroxy-phenyl)-5-methylamino-4-oxo-1H-quinoline-3-carboxamide. LC/MS: m/z 422.5 (M+H)+ at 2.24 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customwas evacuated under vacuum
  2. customby purging with N2
  3. additionMethanol (1 mL) was added
  4. customby evacuating under vacuum
  5. filtrationfiltered through a plug of celite
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-402534f5a46c465e9e8937cc7edee13c
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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