P-Anisidine → HCID 23209265, compound

HRID 1956433Notes

Reaction equation

HRID 1956433 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][N:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>>[OH2:14].[ClH:1].[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:19][C:18]3[CH:20]=[CH:21][C:15]([O:14][CH3:13])=[CH:16][CH:17]=3)=[CH:3][CH:4]=[N:5]2)=[N:10][CH:9]=1

Participants

3

Reactant 2

HCID 7732P-AnisidineHCID 6078223,8-dichloro-1,5-naphthyridine

Product 1

HCID 23209265HCID 23209265, compound

Procedure

A mixture of 4,7-dichloro-1,5-naphthyridine (0.65 g), 4-methoxyaniline (0.40 g) and IMS (25 ml) was boiled under reflux for 5 hours. The mixture was concentrated to approximately 5 ml and then ether added to induce precipitation. Ethyl acetate was added and the solid was collected by filtration to give 7-chloro-4-(4-methoxyanilino)-1,5-naphthyridine hydrochloride hydrate m.p. 230°-233° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. concentrationThe mixture was concentrated to approximately 5 ml
  3. additionether added
  4. customprecipitation
  5. additionEthyl acetate was added
  6. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-43893a38815b4dd0b74492f57d0984a4
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

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