Ethanolamine → 2-(7-Methoxy-6-nitro-quinolin-2-ylamino)-ethanol

HRID 1773563Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=2)[N:3]=1.[NH2:17][CH2:18][CH2:19][OH:20]>O1CCOCC1>[CH3:16][O:15][C:6]1[CH:5]=[C:4]2[C:9]([CH:10]=[CH:11][C:2]([NH:17][CH2:18][CH2:19][OH:20])=[N:3]2)=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-chloro-7-methoxy-6-nitro-quinoline (0.1 g, 0.42 mmol) and 2-aminoethanol (38 μL, 0.63 mmol) in anhydrous 1,4-dioxane (5 mL) was heated at 90° C. overnight. A second aliquot of 2-aminoethanol (38 μL, 0.63 mmol) was added and the resulting mixture was heated at 90° C. overnight. The reaction mixture was then concentrated under reduced pressure, the residue was washed with water, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give 70 mg of 2-(7-methoxy-6-nitro-quinolin-2-ylamino)-ethanol as a solid without further purifications. MS=264 [M+H]+.

Workup

temperaturethe resulting mixture was heated at 90° C. overnight
concentrationThe reaction mixture was then concentrated under reduced pressure
washthe residue was washed with water
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-cdfbbbf85b1f4944a2edb864f7662f47
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255110B2

Reaction notes

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