Lithium Hydroxide → 1-Ethyl-2-(naphthalen-1-yl)-1H-imidazole-4-carboxylic acid

HRID 12460Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)[N:9]([CH2:11][CH3:12])[CH:10]=1)=[O:5])C.[OH-].[Li+]>C1COCC1.O>[CH2:11]([N:9]1[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=[C:8]1[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[CH3:12]

Participants

Conditions

Temperature: 50 °C

Procedure

1-Ethyl-2-naphthalen-1-yl-1H-imidazole-4-carboxylic acid ethyl ester (2.2 g, 7.48 mmol) is dissolved in THF (20 ml), followed by the addition of aqueous lithium hydroxide solution (2.0 N, 7.5 ml, 2.0 eq.). The mixture is heated at 50° C. overnight. THF is stripped off under reduced pressure, and the residue is diluted with water (10 ml), basified to pH=4˜5. The solid precipitate is collected, washed with water and ether, dried under high vacuum to give the title compound. LCMS 267 (M+1).

Workup

customThe solid precipitate is collected
washwashed with water and ether
customdried under high vacuum

Sources & evidence

ORD record: ord-e1d19fefd1aa46a38ad1627104fb90fd
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728009B1

Reaction notes

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