Water → HCID 15239983, compound

HRID 1653639Notes

Reaction equation

HRID 1653639 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[C:5]([O:11][C:12]2[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[N:13]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:34](=[N:37]O)([CH3:36])[CH3:35].O>ClCCl>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][N:37]=[C:34]([CH3:36])[CH3:35])=[O:9])[C:5]([O:11][C:12]2[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[N:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 67180Acetone, oximeHCID 682631,1'-CarbonyldiimidazoleHCID 15239982HCID 15239982, compound

Product 1

HCID 15239983HCID 15239983, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.5 g (5 mmol) of 6-amino-3-[(4,6-dimethoxypyrimidin-2-yl)oxy]picolinic acid, 0.8 g (5 mmol) of carbonyldiimidazole and 0.25 g (3 mmol) of N-isopropylidenehydroxylamine were stirred and refluxed in dichloromethane for 4 hours. After completion of the reaction, the reaction mixture was poured into water, and the dichloromethane layer was separated, washed with water and dried. Then, the solvent was distilled off under reduced pressure. The residual oily product was purified by column chromatography to obtain the desired product as colorless transparent crystals.

Workup

  1. customAfter completion of the reaction
  2. customthe dichloromethane layer was separated
  3. washwashed with water
  4. customdried
  5. distillationThen, the solvent was distilled off under reduced pressure
  6. customThe residual oily product was purified by column chromatography

Sources & evidence

ORD record
ord-2faa2e51949c4721a31c7875be9fe5ba
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

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