Ammonium Hydroxide → 6-(Trifluoromethyl)quinolin-2-amine

HRID 1772276Notes

Reaction equation

HRID 1772276 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=2)[N:3]=1.[OH-].[NH4+:17]>>[F:13][C:12]([F:15])([F:14])[C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH2:17])[CH:11]=[CH:10]2

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 109114112-Chloro-6-(trifluoromethyl)quinoline

Product 1

HCID 112180956-(Trifluoromethyl)quinolin-2-amineYield 38%

Procedure

A solution of 2-chloro-6-(trifluoromethyl)quinoline (1 g, 4.3 mmol) in ammonium hydroxide (50 ml) was stirred overnight at 130° C. The resulting mixture was then concentrated under vacuum to give a residue, which was purified by silica gel column chromatography using 1%˜2% methanol in dichloromethane to afford 6-(trifluoromethyl)quinolin-2-amine as an off-white solid (350 mg, 38%). (ES, m/z): [M+H]+ 212; 1H NMR (300 MHz, CDCl3): δ 7.97-7.86 (m, 2H), 7.71 (s, 2H), 6.85 (d, J=9.0 Hz, 1H), 5.26 (s, 2H).

Workup

  1. concentrationThe resulting mixture was then concentrated under vacuum
  2. customto give a residue, which
  3. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-81e987ee77d34397b89df591172a69b4
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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