Nitric Acid → 5-Hydroxy-6-nitro-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester

HRID 887733Notes

Reaction equation

HRID 887733 reaction equation
[CH3:1][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]([OH:19])[CH:6]=1)=[O:4].[N+:20]([O-])([OH:22])=[O:21].CCCCCC.C(OCC)(=O)C>S(=O)(=O)(O)O>[CH3:1][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:16])[F:17])=[N:12]2)=[C:7]([OH:19])[C:6]=1[N+:20]([O-:22])=[O:21])=[O:4]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 21226206Ethyl acetate hexaneHCID 1361498195-Hydroxy-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester

Product 1

HCID 1361498185-Hydroxy-6-nitro-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

5-Hydroxy-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester (46.0 g) is dissolved in concentrated sulfuric acid (200 mL, 97%) at 0-5° C. To this cooled solution is added drop wise fuming nitric acid (7 mL, 100%). After the addition is complete, the reaction mixture is allowed to warm to room temperature. TLC analysis (hexane/ethyl acetate=4:1) after 30 min shows reaction completion. The reaction mixture is slowly poured onto an ice/water mixture (ca. 2 mL) and the crystals were filtered off, washed thoroughly with water and dried in vacuum to afford 47.0 g of the title compound of the formula

Workup

  1. additionAfter the addition
  2. customreaction completion
  3. filtrationthe crystals were filtered off
  4. washwashed thoroughly with water
  5. customdried in vacuum

Sources & evidence

ORD record
ord-8f94aadd0cb24eb19c5e48f7a06f2ffe
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

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