Ethyl orthoformate → HCID 135741652, compound

HRID 1016193Notes

Reaction equation

HRID 1016193 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([NH2:14])=[O:13])=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.[CH2:15](OC(OCC)OCC)C>>[F:10][C:8]([F:11])([F:9])[C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[CH:15][NH:14][C:12](=[O:13])[C:3]=2[N:4]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 578899673-Amino-6-(trifluoromethyl)picolinamide

Product 1

HCID 135741652HCID 135741652, compoundYield 95.37%

Procedure

6.8 g (0.0332 mol, 1 eq) of 3-amino-6-trifluoromethyl-pyridine-2-carboxylic acid amide in 170 ml of triethylorthoformate under nitrogen was heated at 145° C. for 8 h. Excess triethylorthoformate was removed under reduced pressure and the solid product obtained was washed with pet-ether and dried under vacuum to get 6.8 g (95.37%) of white solid. 1H NMR (CDCl3, 400 MHz): 8.11 (1H, d), 8.35 (1H, d), 12.28 (1H, bs). MS 216 (M+H)+.

Workup

  1. customExcess triethylorthoformate was removed under reduced pressure
  2. customthe solid product obtained
  3. washwas washed with pet-ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-11e1698d908d4030965415e2197ede17
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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