Ammonia → HCID 18451518, compound

HRID 1270777Notes

Reaction equation

HRID 1270777 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.[NH3:17]>C(O)CO>[NH2:17][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 27365914-Chloro-6-fluoro-2-(trifluoromethyl)quinoline

Product 1

HCID 18451518HCID 18451518, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 4-chloro-6-fluoro-2-(trifluoromethyl)quinoline (1 g, 4.01 mmol) and NH3 (3 mL) in ethylene glycol (20 mL) is prepared at −78° C. in a sealed tube. After warming up to room temperature, the sealed tube is gradually heated to 100° C. overnight. After cooling to −78° C., the sealed tube is opened and the contents are concentrated by rotary evaporator. The residue is purified by flash chromatography on silica gel (1:3 EtOAc/hexanes) to give 4-amino-6-fluoro-2-(trifluoromethyl)quinoline as a light yellow solid.

Workup

  1. customis prepared at −78° C. in a sealed tube
  2. temperaturethe sealed tube is gradually heated to 100° C. overnight
  3. temperatureAfter cooling to −78° C.
  4. concentrationthe contents are concentrated by rotary evaporator
  5. customThe residue is purified by flash chromatography on silica gel (1:3 EtOAc/hexanes)

Sources & evidence

ORD record
ord-cc01e814e3294949b9f761a82f0d3e2a
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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