2-Cyclohexylacetaldehyde → 3-Cyclohexyl-quinoline-5-carboxylic acid

HRID 1779953ノート

反応式

HRID 1779953 の反応式
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6](O)[O:7][C:8]2=[O:9])([O-])=O.[CH:15]1([CH2:21][CH:22]=O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C[O-].[Na+]>C(O)(C)C.[Pd].S([O-])([O-])(=O)=O.[Ba+2]>[CH:15]1([C:21]2[CH:22]=[N:1][C:4]3[CH:13]=[CH:12][CH:11]=[C:10]([C:8]([OH:7])=[O:9])[C:5]=3[CH:6]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

参加物

6

反応物 3

HCID 3166272-CyclohexylacetaldehydeHCID 10942334Sodium MethoxideHCID 110955283-hydroxy-4-nitro-3H-isobenzofuran-1-one

生成物 1

HCID 190487293-Cyclohexyl-quinoline-5-carboxylic acid

試薬・触媒・溶媒 2

HCID 16218511Pd barium sulfate触媒HCID 3776Isopropanol溶媒

実験手順

A mixture of 50 g of 4-nitro-3-hydroxyphthalide in 200 ml of isopropanol is hydrogenated with 5 g of Pd/barium sulphate under 3.5 bar, during which the temperature rises to 55° C. When the hydrogenation has ended (about 30 minutes), the catalyst is filtered off hot with suction. 33 g (260 mmol) of cyclohexylacetaldehyde are added to the filtrate and, after addition of a catalytic amount of sodium methylate, the mixture is heated under reflux for 20 hours. After cooling, the crystals which have precipitated out are filtered off with suction and washed with isopropanol. 15 g of virtually colourless product with a melting point of over 280° C. are obtained.

後処理

  1. customrises to 55° C
  2. custom(about 30 minutes)
  3. filtrationthe catalyst is filtered off hot with suction
  4. temperaturethe mixture is heated
  5. temperatureunder reflux for 20 hours
  6. temperatureAfter cooling
  7. customthe crystals which have precipitated out
  8. filtrationare filtered off with suction
  9. washwashed with isopropanol
  10. custom15 g of virtually colourless product with a melting point of over 280° C. are obtained

出典と根拠

ORDレコード
ord-4c55477ba29840a5ab0901dee533f253
出典データセット
uspto-grants-1997_05
特許番号
US05629320

反応ノート

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