Water → N-(2-hydroxy-2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine

HRID 1823381Notes

Reaction equation

HRID 1823381 reaction equation
P(Cl)(Cl)(Cl)=O.[N+:6]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1O)=[N:16][CH:15]=[CH:14][CH:13]=2)([O-:8])=[O:7].O[NH:21][CH2:22][CH:23]([CH3:25])[CH3:24].[OH2:26]>CN(C)C=O.C(O)C>[CH3:24][C:23]([CH3:25])([OH:26])[CH2:22][NH:21][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[N:11]=[CH:10][C:9]=1[N+:6]([O-:8])=[O:7]

Participants

7

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 9543329N-(2-methylpropyl)hydroxylamineHCID 178526774HCID 178526774, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

Phosphorus oxychloride (4 mL, 43 mmol) was reacted with N,N-dimethylformamide (15 mL) while chilling in an ice bath. This mixture was added to a solution of 3-nitro[1,5]naphthyridin-4-ol (6.9 g, 36.1 mmol) in N,N-dimethylformamide (60 mL). The reaction mixture was warmed in an oil bath to 60° C. After 3 hours the reaction mixture was poured into ice water. The resulting precipitate was isolated by filtration and then washed with water. The wet crude 5-chloro-3-nitro[1,5]naphthyridine was suspended in dichloromethane (150 mL). Diisopropylethylamine was added followed by the slow addition of hydroxyisobutylamine (3.4 g, 40 mmol). The reaction mixture was refluxed for 2 hours and then combined with water (˜100 mL). The resulting precipitate was isolated by filtration to provide 7.2 g of 1,1-dimethyl-2-[(3-nitro[]1,5]naphthyridin-4-yl)amino]ethanol. A small sample was recrystallized from isopropanol to provide a pure sample, m.p. 184.5–186° C. Analysis: Calculated for C12H14N4O3: % C, 54.96; % H, 5.38; % N, 21.36; Found: % C, 54.63; % H, 5.36: % N, 21.51.

Workup

  1. temperaturewhile chilling in an ice bath
  2. customThe resulting precipitate was isolated by filtration
  3. washwashed with water
  4. additionDiisopropylethylamine was added
  5. temperatureThe reaction mixture was refluxed for 2 hours
  6. customThe resulting precipitate was isolated by filtration
  7. customA small sample was recrystallized from isopropanol
  8. customto provide a pure sample, m.p. 184.5–186° C

Sources & evidence

ORD record
ord-1d421e923bbd4ed795740a2bf4716105
Source dataset
uspto-grants-2006_05
Patent number
US07038051B2

Reaction notes

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