Hydrochloric Acid → 4,5,8-Trimethyl-6-nitroquinoline

HRID 1598646Notes

Reaction equation

[CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([CH3:12])=[CH:5][C:3]=1[NH2:4].Cl.CO[CH2:16][CH2:17][C:18](OC)(OC)[CH3:19].[OH-].[Na+]>[Cl-].[Zn+2].[Cl-].C(O)C>[N+:9]([C:7]1[C:6]([CH3:12])=[C:5]2[C:3](=[C:2]([CH3:1])[CH:8]=1)[N:4]=[CH:16][CH:17]=[C:18]2[CH3:19])([O-:11])=[O:10]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2,5-dimethyl-4-nitroaniline (0.96 g), ferric chloride hexahydrate (2.50 g), zinc chloride (0.094 g), concentrated hydrochloric acid (0.481 mL), and ethanol (8 mL) is heated to 60° C. 1,3,3-trimethoxybutane (0.73 mL) is added dropwise while the reaction mixture is kept at 60° C. The reaction mixture is heated at reflux overnight and cooled to room temperature. A solution of 10% aqueous sodium hydroxide is added, and the mixture is extracted three times with methylene chloride. The combined organic layers are dried over sodium sulfate, filtered and evaporated to afford a crude product. The crude product is purified by flash chromatography using 25% ethyl acetate in hexane as eluent, providing 6-nitro-4,5,8-trimethylquinoline.

Workup

customis kept at 60° C
temperatureThe reaction mixture is heated
temperatureat reflux overnight
temperaturecooled to room temperature
extractionthe mixture is extracted three times with methylene chloride
dry with materialThe combined organic layers are dried over sodium sulfate
filtrationfiltered
customevaporated
customto afford a crude product
customThe crude product is purified by flash chromatography

Sources & evidence

ORD record: ord-5232e5899cfb43e38c3858ee8996cd17
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739148

Reaction notes

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