Ethyl 5-amino-2-hydroxybenzoate → Ethyl 5-(6-ethoxy-3-ethoxycarbonyl-7-methyl-1,8-naphthyridin-4-ylamino)salicylate hydrochloride

HRID 1956450Notes

Reaction equation

HRID 1956450 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].[NH2:21][C:22]1[CH:32]=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:25]([OH:33])=[CH:24][CH:23]=1>C(O)C>[ClH: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]([O:18][CH2:19][CH3:20])=[O:17])=[C:2]2[NH:21][C:22]1[CH:32]=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:25]([OH:33])=[CH:24][CH:23]=1)[CH3:14]

Participants

4

Reactant 2

HCID 13445456Ethyl 5-amino-2-hydroxybenzoateHCID 23198600Ethyl 4-chloro-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate

Product 1

HCID 23209207Ethyl 5-(6-ethoxy-3-ethoxycarbonyl-7-methyl-1,8-naphthyridin-4-ylamino)salicylate hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-chloro-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate (2.0 g), absolute ethanol (30 ml) and ethyl 5-aminosalicylate (1.23 g) was boiled under reflux for 1 hour. The mixture was cooled to ambient temperature and filtered to give a solid which was recrystallised from IMS to give ethyl 5-(6-ethoxy-3-ethoxycarbonyl-7-methyl-1,8-naphthyridin-4-ylamino)salicylate hydrochloride, m.p. 208°-210° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. filtrationfiltered
  3. customto give a solid which
  4. customwas recrystallised from IMS

Sources & evidence

ORD record
ord-d22229dcbc8c43fa98ad409a0d4469cd
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

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