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Proton sponge → 5-Methoxy-6-nitro-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester

HRID 2039645
Notes
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Reaction equation

HRID 2039645 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])[C:6]=1[N+:20]([O-:22])=[O:21])=[O:4].[CH3:23]N(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.C[O+](C)C.F[B-](F)(F)F>C(Cl)Cl>[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:17])([F:18])[F:16])=[N:12]2)=[C:7]([O:19][CH3:23])[C:6]=1[N+:20]([O-:22])=[O:21])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 88675Proton spongeHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 1361498185-Hydroxy-6-nitro-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester

Product 1

HCID 578559795-Methoxy-6-nitro-2-trifluoromethyl-quinoline-7-carboxylic acid methyl esterYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

A solution of 5-Hydroxy-6-nitro-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester (1.5 g, 4.744 mmol) in methylene chloride is treated with N,N,N′,N′-Tetramethyl-1,8-naphthalendiamine (3.05 g, 14.232 mmol) and Trimethyloxonium-tetrafluorborate (2.11 g, 14.232 mmol) at 0-5° C. under argon. The reaction mixture is allowed to warm to room temperature with stirring. The reaction is complete after 2.5 hr as shown by TLC analysis. The reaction mixture is diluted with methylene chloride, and then washed successively with 2N aqueous hydrochloric acids, water, and brine. The organic phase is dried over anhydrous sodium sulphate, filtered, and concentrated in vacuo. The residue (2.9 g) is purified by flash column chromatography, eluting with 3:1 hexane:ethyl acetate. This gives the title compound (1.2 g, 76%) as yellow crystals.

Workup

  1. washwashed successively with 2N aqueous hydrochloric acids, water, and brine
  2. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue (2.9 g) is purified by flash column chromatography
  6. washeluting with 3:1 hexane

Sources & evidence

ORD record
ord-fd7f8ecf4f724db2b600d92ca8a9d40b
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08580785B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes