1-Naphthalenemethanamine → HCID 178470173, compound

HRID 1595335Notes

Reaction equation

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

Participants

Reactant 2

HCID 83551-Naphthalenemethanamine

HCID 178472890HCID 178472890, compound

Product 1

HCID 178470173HCID 178470173, compoundYield 41.3%

Procedure

Ethyl 2-hydroxyimino-3-phenyl-3-oxopropionate (10.0 g) and 1-aminomethylnaphthalene (7.8 g) were reacted and treated in the same manner as in Starting Material Synthetic Example 1 to give ethyl 2-(1-naphthyl)-5-phenylimidazole-4-carboxylate (6.4 g). 6.0 g therefrom was dissolved in ethyl alcohol (120 ml) and 1 M sodium hydroxide solution (45 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-phenylimidazole-4carboxyic acid (4.1 g), melting point 172° C. (decomposition).

Workup

additiontreated in the same manner as

Sources & evidence

ORD record: ord-5a6883fcf5ee40bb82cba97fee519e8e
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288061B1

Reaction notes

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