Hydrochloric Acid → HCID 57855965, compound

HRID 2039635Notes

Reaction equation

HRID 2039635 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, compound

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, 12.03 mmol) are dissolved in 200 ml of methanol/water (3:1 mixture), and treated with lithium hydroxide hydrate (1.06 g, 0.046 mol) at room temperature. After reaction completion the mixture is poured into ethyl acetate and 2 N hydrochloric acid, the organic phase is washed three times with water, dried with sodium sulphate, filtered and concentrated in vacuo. The residue is triturated with a little hexane. Filtration gives 3.50 g (97% of theory) of the title compound as white crystals. 1H NMR (d6-DMSO3, 400 MHz): δ ppm: 2.65 (s, 3H); 8.25 (d, 1H); 8.56 (s, 1H); 9.05 ppm (d, 1H).

Workup

  1. customAfter reaction completion the mixture
  2. washthe organic phase is washed three times with water
  3. dry with materialdried with sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is triturated with a little hexane
  7. filtrationFiltration

Sources & evidence

ORD record
ord-435abac5c4fe471abcfa9140db22385d
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

Loading…