Trifluoroacetic acid → 5-(Benzyloxy)-2-(hydrazinocarbonyl)-4-oxo-1,4-dihydropyridine

HRID 1252597Notes

Reaction equation

HRID 1252597 reaction equation
CC(C)(OC([NH:7][NH:8][C:9]([C:11]1[NH:12][CH:13]=[C:14]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15](=[O:17])[CH:16]=1)=[O:10])=O)C.FC(F)(F)C(O)=O>>[O:17]=[C:15]1[C:14]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:13][NH:12][C:11]([C:9]([NH:8][NH2:7])=[O:10])=[CH:16]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 141824661,4-Dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinecarboxylic acid, 2-[(1,1-dimethylethoxy)carbonyl]-hydrazide

Product 1

HCID 141824695-(Benzyloxy)-2-(hydrazinocarbonyl)-4-oxo-1,4-dihydropyridineYield 137.7%

Procedure

1,4-Dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinecarboxylic acid, 2-[(1,1-dimethylethoxy)carbonyl]hydrazide (69 g, 0.191 mol) was added at 0° C. to 370 ml of trifluoroacetic acid. The mixture was stirred for 1 hour at room temperature, then evaporated. The remaining syrup was treated with ether to yield 68.2 g of crude 1,4-dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinecarboxylic acid, hydrazide, trifluoroacetate (1:2) salt as a solid.

Workup

  1. customevaporated
  2. additionThe remaining syrup was treated with ether

Sources & evidence

ORD record
ord-2d01d4c17cd0405ab95e911ae96ee345
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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