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

HRID 1590662ノート

反応式

HRID 1590662 の反応式
[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

参加物

6

反応物 4

HCID 795ImidazoleHCID 5462222PotassiumHCID 67086713Potassium imidazoleHCID 867467395,6-Dihydro-7,8-epoxy-8-methyl-2-naphthalenecarboxylic acid

生成物 1

HCID 197679765,6,7,8-tetrahydro-8-hydroxy-8-methyl-7-(1H-imidazol-1-yl)-2-naphthalenecarboxylic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
130 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-b5e8fa7456594e0c97f219176c50b0e1
出典データセット
uspto-grants-1993_04
特許番号
US05204364

反応ノート

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