Hydrochloric Acid → HCID 57855965, compound

HRID 887735Notes

Reaction equation

HRID 887735 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([C:15]([F:18])([F:17])[F:16])=[N:12]2)=[C:7]([CH3:19])[C:6]=1[N+:20]([O-:22])=[O:21])=[O:4].O.[OH-].[Li+].C(OCC)(=O)C.Cl>CO.O>[CH3:19][C:7]1[C:6]([N+:20]([O-:22])=[O:21])=[C:5]([C:3]([OH:4])=[O:2])[CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11]([C:15]([F:17])([F:16])[F:18])=[N:12]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 57855969HCID 57855969, compound

Product 1

HCID 57855965HCID 57855965, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

5-Methyl-6-nitro-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester (3.78 g) is dissolved in 200 mL of methanol/water (3:1 mixture) and treated with lithium hydroxide hydrate (1.06 g) at room temperature. After reaction completion, the mixture is poured into ethyl acetate and 2N hydrochloric acid, the organic phase is washed 3× with water, dried over sodium sulfate, filtered and concentrated in vacuum. The residue is triturated with a small amount of hexane. Filtration gives 3.50 g of the title compound of the formula

Workup

  1. customAfter reaction completion
  2. washthe organic phase is washed 3× with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customThe residue is triturated with a small amount of hexane
  7. filtrationFiltration

Sources & evidence

ORD record
ord-e7ac2e55f1174bafa4e462088fad5885
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

Loading…