P-Anisidine → Ethyl 4-(4-methoxyanilino)-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate hydrochloride

HRID 128623Notes

Reaction equation

HRID 128623 reaction equation
[Cl:1][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]([O:18][CH2:19][CH3:20])=[O:17].[CH3:21][O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1>C(O)C>[ClH:1].[CH3:21][O:22][C:23]1[CH:29]=[CH:28][C:26]([NH:27][C:2]2[C:11]3[C:6](=[N:7][C:8]([CH3:15])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 23198600Ethyl 4-chloro-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate

Product 1

HCID 19374282Ethyl 4-(4-methoxyanilino)-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-chloro-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate (3.5 g) and 4-methoxyaniline (1.5 g) in ethanol (50 ml) was boiled under reflux for 1.5 hours. The reaction mixture was concentrated to half the volume, cooled and ether added. The solid was collected by filtration and dried to give ethyl 4-(4-methoxyanilino)-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate hydrochloride m.p. 260°-262° C. (with decomposition).

Workup

  1. temperatureunder reflux for 1.5 hours
  2. concentrationThe reaction mixture was concentrated to half the volume
  3. temperaturecooled
  4. additionether added
  5. filtrationThe solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-dfe5f9b5be2f40219149bde7e0d8cd62
Source dataset
uspto-grants-1995_11
Patent number
US05464781

Reaction notes

Loading…