Glycerol → 6-Ethoxy-8-nitroquinoline

HRID 513388Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)[CH3:2].O[CH2:15][CH:16]([CH2:18]O)O.[Na+].[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O>>[CH2:1]([O:3][C:4]1[CH:10]=[C:9]2[C:7](=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)[N:8]=[CH:18][CH:16]=[CH:15]2)[CH3:2]

Participants

Reactant 3

HCID 753Glycerol

HCID 31389Sodium 3-nitrobenzenesulfonate

HCID 692294-Ethoxy-2-nitroaniline

Product 1

HCID 167725846-Ethoxy-8-nitroquinolineYield 75.1%

Procedure

In a similar fashion using route 10 general procedure 20, 4-ethoxy-2-nitroaniline (1.0 g, 5.49 mmol), glycerol (1.6 g, 17.0 mmol) and 3-nitrobenzenesulfonic acid sodium salt (1.6 g, 7.14 mmol) gave the title compound (900 mg, 75%) which was used in the next step without purification.

Sources & evidence

ORD record: ord-be2536717f0944b4848386e98ba22d9d
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

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