P-Anisidine → HCID 23209186, compound

HRID 1956444Notes

Reaction equation

HRID 1956444 reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][C:8]([CH3:15])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[CH3:18][O:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1>>[CH2:13]([O:12][C:9]1[CH:10]=[C:11]2[C:6](=[N:7][C:8]=1[CH3:15])[N:5]=[CH:4][C:3]([C:16]#[N:17])=[C:2]2[NH:24][C:23]1[CH:25]=[CH:26][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1)[CH3:14]

Participants

3

Reactant 2

HCID 7732P-AnisidineHCID 23209213HCID 23209213, compound

Product 1

HCID 23209186HCID 23209186, compound

Procedure

A mixture of 4-chloro-6-ethoxy-7-methyl-1,8-naphthyridine-3-carbonitrile (2.66 g), 4-methoxyaniline (1.35 g) and IMS (50 ml) was boiled under reflux for 2.5 hours. The mixture was cooled in ice and the precipitate was collected by filtration. This solid was boiled in IMS (50 ml), with 5M sodium hydroxide solution (1.2 ml) under reflux for 30 minutes. The mixture was cooled and evaporated. The residue was purified by flash chromatography on silica using dichloromethane/IMS, 19:1 as the mobile phase to give a solid which was ground up in IMS (15 ml) and filtered to give 6-ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridine-3-carbonitrile, m.p. 190°-192° C. Active (1/1) at 30 mg/kg.

Workup

  1. temperatureunder reflux for 2.5 hours
  2. temperatureThe mixture was cooled in ice
  3. filtrationthe precipitate was collected by filtration
  4. temperatureunder reflux for 30 minutes
  5. temperatureThe mixture was cooled
  6. customevaporated
  7. customThe residue was purified by flash chromatography on silica
  8. customto give a solid which
  9. filtrationfiltered

Sources & evidence

ORD record
ord-354fdc7f5f6041f893dbaf6265ee1dbd
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

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