Glycerol → HCID 18465378, compound

HRID 1901250Notes

Reaction equation

HRID 1901250 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 (6×300 mL). 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 (6×300 mL)
  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-125c6bed686c4a61870390012212a01c
Source dataset
uspto-grants-1996_11
Patent number
US05576437

Reaction notes

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