2-Methoxyaniline → 3-Ethoxy-5-(2-methoxyanilino)-2-methyl-1,8-naphthyridine hydrochloride

HRID 128624Notes

Reaction equation

HRID 128624 reaction equation
[Cl:1][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][CH:22]=[CH:21][C:19]=1[NH2:20]>>[ClH:1].[CH2:14]([O:13][C:5]1[C:6]([CH3:12])=[N:7][C:8]2[C:3]([CH:4]=1)=[C:2]([NH:20][C:19]1[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=1[O:17][CH3:16])[CH:11]=[CH:10][N:9]=2)[CH3:15]

Participants

3

Reactant 2

HCID 70002-MethoxyanilineHCID 193742665-Chloro-3-ethoxy-2-methyl-1,8-naphthyridine

Product 1

HCID 193743573-Ethoxy-5-(2-methoxyanilino)-2-methyl-1,8-naphthyridine hydrochloride

Procedure

In a similar manner to Example 1, a mixture of 5-chloro-3-ethoxy-2-methyl-1,8-naphthyridine (2.0 g) and 2-methoxyaniline (1.05 g) in IMS (30 ml) was boiled under reflux for 6 hours then cooled and filtered to give 3-ethoxy-5-(2-methoxyanilino)-2-methyl-1,8-naphthyridine hydrochloride, m.p. 250°-252° C. (with decomposition). Active (1/1) at 30 mg/kg.

Workup

  1. temperatureunder reflux for 6 hours
  2. temperaturethen cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-3493ab135bd94e218c9a1ad37113aa48
Source dataset
uspto-grants-1995_11
Patent number
US05464781

Reaction notes

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