Imidazole → 5,6,7,8-tetrahydro-8-hydroxy-8-methyl-7-(1H-imidazol-1-yl)-2-naphthalenecarboxylic acid

HRID 1590662Notes

Reaction equation

[O:1]1[C:11]2([CH3:12])[CH:2]1[CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:13]([OH:15])=[O:14])=[CH:9][C:10]=12.[K].[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.N1C=CN=C1.[K]>CN(C=O)C>[OH:1][C:11]1([CH3:12])[C:10]2[CH:9]=[C:8]([C:13]([OH:15])=[O:14])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3][CH:2]1[N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

Conditions

Temperature: 130 °C

Procedure

A solution of 1.9 g of 5,6-dihydro-7,8-epoxy-8-methyl-2-naphthalenecarboxylic acid (prepared by epoxidation of 5,6-dihydro-8-methyl-2-naphthalenecarboxylic acid, m.p. 150°-153° C.) in anhydrous DMF is added to a solution of imidazole potassium salt, prepared from prepared from 3.16 g of imidazole and 1.81 g of potassium, in anhydrous DMF (100 ml) and heated at 130° C., with vigorous stirring, for 6 hours. The solvent is evaporated under reduced pressure and the residue is taken up with water and ethyl acetate. The aqueous layer is separated and acidified to pH=5 with acetic acid. The water is evaporated under vacuum and the residue is chromatographed on silica gel (eluent CHCl3 :CH3OH, 70:30) giving 1.6 g of 5,6,7,8-tetrahydro-8-hydroxy-8-methyl-7-(1H-imidazol-1-yl)-2-naphthalenecarboxylic acid.

Workup

customprepared
customThe solvent is evaporated under reduced pressure
customThe aqueous layer is separated
customThe water is evaporated under vacuum
customthe residue is chromatographed on silica gel (eluent CHCl3 :CH3OH, 70:30)

Sources & evidence

ORD record: ord-b5e8fa7456594e0c97f219176c50b0e1
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05204364

Reaction notes

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