Trifluoroacetic acid → 5-Cyano-3-methylpyridine-2-carboxylic acid

HRID 474118Notes

Reaction equation

HRID 474118 reaction equation
C([O:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][C:11]([C:15]#[N:16])=[CH:10][N:9]=1)=[O:7])(C)(C)C.COC1C=CC=C(OC)C=1.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1>[C:15]([C:11]1[CH:12]=[C:13]([CH3:14])[C:8]([C:6]([OH:7])=[O:5])=[N:9][CH:10]=1)#[N:16]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 90251,3-DimethoxybenzeneHCID 666658265-Cyano-3-methyl-pyridine-2-carboxylic acid tert-butyl ester

Product 1

HCID 666658465-Cyano-3-methylpyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5-cyano-3-methyl-pyridine-2-carboxylic acid tert-butyl ester (8.50 g, 38.9 mmol) in 1,3-dimethoxybenzene (51 ml, 389 mmol) was added TFA (85 ml) and stirred for 6.5 h. The reaction mixture was diluted with toluene and evaporated. The residue was taken up in toluene and evaporated (2×). The product was crystallized from TBME/hexanes to give the title compound as a white powder. HPLC: RtH1=2.314 min; ESIMS [M+Na]+=163; 1H-NMR (360 MHz, CDCl3): δ 8.77 (s, 1H), 8.07 (s, 1H), 2.87 (s, 3H).

Workup

  1. customevaporated
  2. customevaporated (2×)
  3. customThe product was crystallized from TBME/hexanes

Sources & evidence

ORD record
ord-c869662d9b404fa7a0a00a9333644066
Source dataset
uspto-grants-2014_01
Patent number
US08637508B2

Reaction notes

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