Glycerol → HCID 18465378, compound

HRID 861935Notes

Reaction equation

HRID 861935 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[CH3:12].O.[As+3]=O.S(=O)(=O)(O)O.[OH-].[NH4+].O[CH2:24][CH:25]([CH2:27]O)O>O>[NH2:1][C:2]1[C:3]([CH3:12])=[C:4]2[C:5]([CH:24]=[CH:25][CH:27]=[N:9]2)=[C:6]([F:8])[CH:7]=1

Participants

7

Reactant 5

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 184653775-Fluoro-2-methyl-3-nitroanilineHCID 178526933HCID 178526933, compound

Product 1

HCID 18465378HCID 18465378, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-amino-4-fluoro-6-nitrotoluene (4.4 g), glycerin (7.5 g), arsenic(V) oxide hydrate (Aldrich, 54% in arsenic, 5.0 g), and concentrated sulfuric acid (35 mL) is heated to 140° C. for 4 hours. The reaction is allowed to cool to room temperature and diluted with water (300 mL). The mixture is basified with concentrated ammonium hydroxide to pH=10 and extracted with ethyl acetate (6×300mL). The combined extracts are dried over sodium sulfate and rotary evaporated. The crude product is purified by flash chromatography on silica gel, eluting with 25% ethyl acetate/hexane to afford 7-amino-5-fluoro-8-methylquinoline as a solid.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate (6×300mL)
  3. dry with materialThe combined extracts are dried over sodium sulfate and rotary evaporated
  4. customThe crude product is purified by flash chromatography on silica gel
  5. washeluting with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a755083ffb1c4408bc3db2bf5237cc6e
Source dataset
uspto-grants-1998_02
Patent number
US05716966

Reaction notes

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