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

HRID 2120820Notes

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>[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

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

temperaturewhile chilling in an ice bath
customThe resulting precipitate was isolated by filtration
washwashed with water
additionDiisopropylethylamine was added
temperatureThe reaction mixture was refluxed for 2 hours
customThe resulting precipitate was isolated by filtration

Sources & evidence

ORD record: ord-7ebcddc149e642eea2a1f127a6ae0daf
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06693113B2

Reaction notes

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