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

HRID 1590662노트

반응식

HRID 1590662 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
130 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b5e8fa7456594e0c97f219176c50b0e1
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05204364

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