P-Anisidine → 3-Ethoxy-5-(4-methoxyanilino)-2-methyl-1,8-naphthyridine hydrate

HRID 1956436Notes

Reaction equation

HRID 1956436 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([O:13][CH2:14][CH3:15])[C:6]([CH3:12])=[N:7]2.[CH3:16][O:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.[OH-].[Na+]>O>[OH2:13].[CH2:14]([O:13][C:5]1[C:6]([CH3:12])=[N:7][C:8]2[C:3]([CH:4]=1)=[C:2]([NH:22][C:21]1[CH:23]=[CH:24][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1)[CH:11]=[CH:10][N:9]=2)[CH3:15]

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 14798Sodium HydroxideHCID 193742665-Chloro-3-ethoxy-2-methyl-1,8-naphthyridine

Product 1

HCID 232092353-Ethoxy-5-(4-methoxyanilino)-2-methyl-1,8-naphthyridine hydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 5-chloro-3-ethoxy-2-methyl-1,8-naphthyridine (5.0 g), 4-methoxyaniline (2.77 g) and IMS (40 ml) was boiled under reflux for 2.5 hours. The mixture was cooled and filtered. The solid obtained was dissolved in boiling IMS (50 ml) and 5M sodium hydroxide solution (4.0 ml) was added. The mixture was heated under reflux for 1 hour and then cooled and water (100 ml) was added. The mixture was filtered to give 3-ethoxy-5-(4-methoxyanilino)-2-methyl-1,8-naphthyridine hydrate, m.p. 228°-231° C.

Workup

  1. temperatureunder reflux for 2.5 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customThe solid obtained
  5. dissolutionwas dissolved
  6. additionwas added
  7. temperatureThe mixture was heated
  8. temperatureunder reflux for 1 hour
  9. temperaturecooled
  10. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-8eabe4fb124348e4bc8c9fd6fcf6d758
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

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