Glycerol → 7-Methoxyquinoline

HRID 513409Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].O[CH2:11][CH:12]([CH2:14]O)O.[Na+].[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O.OS(O)(=O)=O.O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:7]([CH:11]=[CH:12][CH:14]=[N:6]2)=[CH:8][CH:9]=1

Participants

Reactant 4

HCID 753Glycerol

HCID 108243-Methoxyaniline

HCID 31389Sodium 3-nitrobenzenesulfonate

HCID 21910475Sulfuric acid hydrate (1:1)

Product 1

HCID 786667-MethoxyquinolineYield 14%

Procedure

In a similar fashion using route 10 general procedure 20, 3-methoxyaniline (1.0 g, 8.12 mmol), glycerol (2.32 g, 25.2 mmol), 3-nitrobenzenesulfonic acid sodium salt (2.4 g, 10.6 mmol) and H2SO4/H2O (6 ml, 7:5) gave the title compound (170 mg, 14%) after purification by column chromatography with n-hexane/EtOAc (17:3) as the eluent.

Sources & evidence

ORD record: ord-6814edb5830d44ef92a477e77bee47d9
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

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