Pyridine → HCID 178432383, compound

HRID 1075754

Reaction equation

HRID 1075754 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][C:8](C)=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1C(O)=O.F[C:17](F)(F)[C:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:19].N1C=CC=C[CH:33]=1>>[N+:27]([C:24]1[CH:25]=[CH:26][C:21]([O:20][C:18]([C:17]2[C:4]([CH3:3])=[N:5][C:6]3[C:11]([C:2]=2[OH:1])=[C:10]([CH3:33])[CH:9]=[CH:8][N:7]=3)=[O:19])=[CH:22][CH:23]=1)([O-:29])=[O:28]

Participants

4

Reactant 3

HCID 1049PyridineHCID 695694-Nitrophenyl trifluoroacetateHCID 178422970HCID 178422970, compound

Product 1

HCID 178432383HCID 178432383, compound

Conditions

Temperature
55 °C

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--methyl--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=0 1700 cm-1 ; νNO2 1520 cm-1, 1345 cm-1.

Workup

  1. stirringstirring
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-d026d38346d84915ae3f8aafb3a3a39f
Source dataset
uspto-grants-1976_05
Patent number
US03954733

Linked notes

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