2-(4-aminophenoxy)acetamide → Ethyl 4-[4-(carbamoylmethoxy)anilino]-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate hydrochloride

HRID 1956445Notes

Reaction equation

HRID 1956445 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]=[CH:31][C:25]([O:26][CH2:27][C:28]([NH2:30])=[O:29])=[CH:24][CH:23]=1>C(O)C>[ClH:1].[C:28]([CH2:27][O:26][C:25]1[CH:31]=[CH:32][C:22]([NH:21][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:23][CH:24]=1)(=[O:29])[NH2:30]

Participants

4

Reactant 2

HCID 30260062-(4-aminophenoxy)acetamideHCID 23198600Ethyl 4-chloro-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate

Product 1

HCID 23209291Ethyl 4-[4-(carbamoylmethoxy)anilino]-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 (2.0 g), 4-aminophenoxy acetamide (1.13 g) and absolute ethanol (30 ml) was boiled under reflux for 1 hour and then cooled to ambient temperature. The mixture was filtered to give ethyl 4-[4-(carbamoylmethoxy)anilino]-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate hydrochloride, m.p. 215°-217° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-7f598e637b0145d69078de8a302c44bf
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

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