1-Naphthalenemethanamine → HCID 178470175, compound

HRID 1595336Notes

Reaction equation

O[N:2]=[C:3]([C:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:21][CH2:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1>>[C:23]1([C:22]2[NH:21][C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:2]=2)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1

Participants

Reactant 2

HCID 83551-Naphthalenemethanamine

HCID 178472893HCID 178472893, compound

Product 1

HCID 178470175HCID 178470175, compoundYield 30.1%

Procedure

Ethyl 2-hydroxyimino-3-(4-trifluoromethylphenyl)-3-oxopropionate (15.0 g) and 1-aminomethylnaphthalene (9.6 g) were reacted and treated in the same manner as in Starting Material Synthetic Example 1 to give ethyl 2-(1-naphthyl)-5-(4-trifluoromethyl-phenyl)imidazole-4-carboxylate (6.4 g). 5.0 g therefrom was dissolved in ethyl alcohol (100 ml) and 1 M sodium hydroxide solution (30 ml) was added. The mixture was reacted and treated in the same manner as in Starting Material Synthetic Example 2 to give 2-(1-naphthyl)-5-(4-trifluoromethylphenyl)imidazole-4-carboxyic acid (3.4 g), melting point 166° C. (decomposition).

Workup

additiontreated in the same manner as

Sources & evidence

ORD record: ord-bca8e7d51c314f05aa5ae73af6b3374c
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288061B1

Reaction notes

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