Water → 3-[(7-Bromo-3-nitro[1,5]naphthyridin-4-yl)amino]propan-1-ol

HRID 1187422Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](Cl)=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[N:4][CH:3]=1.C(N(CC)CC)C.[NH2:23][CH2:24][CH2:25][CH2:26][OH:27].O>ClCCl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[N:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 7-bromo-4-chloro-3-nitro[l,5]naphthyridine (22.53 g, 78.10 g) in dichloromethane (260 mL) at room temperature was added triethylamine (14.2 mL, 102 mmol). The solution was cooled to 0° C. and 3-amino-1-propanol (6.57 mL, 85.9 mmol) was added. The solution was stirred for 20 minutes at room temperature and then was concentrated under reduced pressure to yield a yellow solid. Water (250 mL) was added to the solid, and the mixture was sonicated for 10 minutes. The solid was isolated by filtration, washed with water, and dried at 70° C. under vacuum to afford 22.60 g of 3-[(7-bromo-3-nitro[1,5]naphthyridin-4-yl)amino]propan-1-ol as a yellow powder.

Workup

concentrationwas concentrated under reduced pressure
customto yield a yellow solid
customthe mixture was sonicated for 10 minutes
customThe solid was isolated by filtration
washwashed with water
customdried at 70° C. under vacuum

Sources & evidence

ORD record: ord-a151a453e2b3490bb1e7cf14b7d3f562
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673932B2

Reaction notes

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