Sodium Hydroxide → HCID 10469344, compound

HRID 1656429Notes

Reaction equation

HRID 1656429 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][C:10]([C:20]([F:23])([F:22])[F:21])=[CH:9][CH:8]=2)([O-])=O.[OH-].[Na+]>Cl>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][C:10]([C:20]([F:23])([F:21])[F:22])=[CH:9][CH:8]=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15035173HCID 15035173, compound

Product 1

HCID 10469344HCID 10469344, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 3-nitro-4-phenyl-6-trifluoromethylquinoline (2.0 g), stannous chloride dihydrate (5.0 g) and conc. hydrochloric acid (20 ml) was stirred for 1 hr. at 100° C. The mixture was neutralized with 6N-sodium hydroxide solution and extracted with chloroform. The chloroform layer was washed with water, dried over anhydrous magnesium sulfate, and then distilled to remove the solvent. The residue was recrystallized from a mixture of isopropyl ether and hexane to give 3-amino-4-phenyl-6-trifluoromethylquinoline (1.46 g, 80 %). m.p. 107°-108° C.

Workup

  1. customat 100° C
  2. extractionextracted with chloroform
  3. washThe chloroform layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue was recrystallized from a mixture of isopropyl ether and hexane

Sources & evidence

ORD record
ord-c6ff511429bf4917b6236254a9de1818
Source dataset
uspto-grants-1993_10
Patent number
US05254565

Reaction notes

Loading…