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

HRID 1595337Notes

Reaction equation

O[N:2]=[C:3]([C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:18][CH2:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1>>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[NH:18][C:19]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][CH:21]=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 178472897HCID 178472897, compound

Product 1

HCID 178470177Ethyl 5-(4-fluorophenyl)-2-(1-naphthyl)imidazole-4-carboxylateYield 21.9%

Procedure

Ethyl 2-hydroxyimino-3-(4-fluorophenyl)-3-oxopropionate (10.0 g) and 1-aminomethylnaphthalene (8.3 g) were reacted and treated in the same manner as in Starting Material Synthetic Example 1 to give ethyl 5-(4-fluorophenyl)-2-(1-naphthyl)imidazole-4-carboxylate (3.3 g). 3.0 g therefrom was dissolved in ethyl alcohol (100 ml) and 1 M sodium hydroxide solution (20 ml) was added. The mixture was reacted and treated in the same manner as in Starting Material Synthetic Example 2 to give 5-(4-fluorophenyl)-2-(1-naphthyl)imidazole-4-carboxyic acid (2.4 g), melting point 175° C. (decomposition).

Workup

additiontreated in the same manner as

Sources & evidence

ORD record: ord-fd6964b25c2a4708b4177a9817ac1d20
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288061B1

Reaction notes

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