4-Nitrophenyl trifluoroacetate → HCID 178422968, compound

HRID 1415112Notes

Reaction equation

HRID 1415112 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]([OH:15])=[O:14].FC(F)(F)C(O[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=O>N1C=CC=CC=1>[N+:27]([C:24]1[CH:25]=[CH:26][C:21]([O:14][C:13]([C:3]2[CH:4]=[N:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][CH:9]=[C:8]([CH3:12])[N:7]=3)=[O:15])=[CH:22][CH:23]=1)([O-:29])=[O:28]

Participants

4

Reactant 2

HCID 695694-Nitrophenyl trifluoroacetateHCID 178422970HCID 178422970, compound

Product 1

HCID 178422968HCID 178422968, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1 g of 4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylic acid and 25 ml of anhydrous pyridine was heated on an oil bath at 50° to 60° C while stirring. Then, 1.38 g of p-nitrophenyl trifluoroacetate were added thereto and, after the heating was interrupted, stirring was carried out for 2 hours. The precipitated crystals were collected by filtration and washed with ethanol to give 4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylic acid p-nitrophenyl ester as pale yellow crystalline powder melting at 311 to 313° C (decomp.). Yield, 1.2 g. IR νC=O 1700 cm-1 ; νNO2 1520 cm-1, 1345 cm-1.

Workup

  1. temperaturewas heated on an oil bath at 50° to 60° C
  2. stirringstirring
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-09aec5f9a3b04c94a0c6b37533d15390
Source dataset
uspto-grants-1977_01
Patent number
US04003887

Reaction notes

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