Glycerol → 5,6-Dimethyl-8-nitroquinoline

HRID 513395Notes

Reaction equation

HRID 513395 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.O[CH2:14][CH:15]([CH2:17]O)O.[Na+].[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O.OS(O)(=O)=O.O>>[CH3:9][C:8]1[C:2]([CH3:1])=[CH:3][C:4]([N+:10]([O-:12])=[O:11])=[C:5]2[C:7]=1[CH:14]=[CH:15][CH:17]=[N:6]2

Participants

5

Reactant 4

HCID 753GlycerolHCID 31389Sodium 3-nitrobenzenesulfonateHCID 814454,5-Dimethyl-2-nitrobenzenamineHCID 21910475Sulfuric acid hydrate (1:1)

Product 1

HCID 1104645,6-Dimethyl-8-nitroquinolineYield 16.5%

Procedure

In a similar fashion using route 10 general procedure 20, 4,5-dimethyl-2-nitroaniline (1.0 g, 6.0 mmol), glycerol (1.0 g, 11.4 mmol), 3-nitrobenzenesulfonic acid sodium salt (2.2 g, 9.6 mmol) and H2SO4/H2O (3 ml, 7:1), further reagents added over 4 days, gave the title compound (200 mg, 16%) which was used in the next step without purification.

Workup

  1. additionadded over 4 days

Sources & evidence

ORD record
ord-2bc6e920bddf4f368ea54ec7ee8a4292
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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