N-(2-hydroxy-2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine → 1,1-Dimethyl-2-[(3-amino[1,5]naphthyridin-4-yl)amino]ethanol

HRID 2120821Notes

Reaction equation

HRID 2120821 reaction equation
[CH3:1][C:2]([CH3:19])([OH:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[N:8]=[CH:7][C:6]=1[N+:15]([O-])=O.[H][H]>[Pt].C(O)(C)C>[CH3:1][C:2]([CH3:19])([OH:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[N:8]=[CH:7][C:6]=1[NH2:15]

Participants

5

Reactant 2

HCID 22172695N-(2-hydroxy-2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 221726871,1-Dimethyl-2-[(3-amino[1,5]naphthyridin-4-yl)amino]ethanol

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 3776IsopropanolSolvent

Procedure

A catalytic amount of 5% platinum on carbon was added to a suspension of 1,1-dimethyl-2-[(3-nitro[1,5]naphthyridin-4-yl)amino]ethanol (7 g, 26 mmol) in isopropanol (300 mL). The mixture was hydrogenated on a Parr apparatus at 50 psi (3.5 Kg/cm2) hydrogen pressure for 3 hours. The reaction mixture was fileted to remove the catalyst. The filtrate was concentrated under vacuum. Toluene was added to the residue and the mixture was concentrated under vacuum to remove all of the alcohol and provide crude 1,1-dimethyl-2-[(3-amino[1,5]naphthyridin-4-yl)amino]ethanol.

Workup

  1. customto remove the catalyst
  2. concentrationThe filtrate was concentrated under vacuum
  3. additionToluene was added to the residue
  4. concentrationthe mixture was concentrated under vacuum
  5. customto remove all of the alcohol

Sources & evidence

ORD record
ord-70aa55ce15a54ba69e3ecf7469beb32d
Source dataset
uspto-grants-2004_02
Patent number
US06693113B2

Reaction notes

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