1-Naphthalenemethanamine → Ethyl 5-(4-methoxyphenyl)-2-(l-naphthyl)imidazole-4-carboxylate

HRID 1595334Notes

Reaction equation

O[N:2]=[C:3]([C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:19][CH2:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1>>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[NH:19][C:20]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)=[N:2][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:12][CH:13]=1

Participants

Reactant 2

HCID 83551-Naphthalenemethanamine

HCID 178472900HCID 178472900, compound

Product 1

HCID 178470179Ethyl 5-(4-methoxyphenyl)-2-(l-naphthyl)imidazole-4-carboxylateYield 35.1%

Procedure

Ethyl 2-hydroxyimino-3-(4-methoxyphenyl)-3-oxopropionate (10.0 g) and 1-aminomethylnaphthalene (7.5 g) were reacted and treated in the same manner as in Starting Material Synthetic Example 1 to give ethyl 5-(4-methoxyphenyl)-2-(l-naphthyl)imidazole-4-carboxylate (5.2 g). 5.0 g therefrom was dissolved in ethyl alcohol (300 ml), and 1 M sodium hydroxide solution (50 ml) was added. The mixture was reacted and treated in the same manner as in Starting Material Synthetic Example 2 to give 5-(4-methoxyphenyl)-2-(1-naphthyl)imidazole-4-carboxyic acid (3.9 g), melting point 178° C. (decomposition).

Workup

additiontreated in the same manner as

Sources & evidence

ORD record: ord-a9491b37276b4ac3bd3f518260b30ea1
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288061B1

Reaction notes

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