3-Aminobenzoic Acid → 2-Methyl-5-quinolinecarboxylic acid

HRID 718689ノート

反応式

HRID 718689 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[Na+].[N+]([C:15]1[CH:16]=C(S([O-])(=O)=O)C=[CH:19][CH:20]=1)([O-])=O.C(=O)/C=C/C>Cl>[CH3:19][C:20]1[CH:15]=[CH:16][C:3]2[C:4]([C:5]([OH:7])=[O:6])=[CH:8][CH:9]=[CH:10][C:2]=2[N:1]=1

参加物

5

反応物 3

HCID 74193-Aminobenzoic AcidHCID 31389Sodium 3-nitrobenzenesulfonateHCID 447466Crotonaldehyde

生成物 1

HCID 3199762-Methyl-5-quinolinecarboxylic acid

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

反応条件

温度
90 °C

実験手順

A mixture of 3-aminobenzoic acid (9.0 g, 65 mmol), ferrous sulfate heptahydrate (5.2 g, 18 mmol) and 3-nitrobenzenesulfonic acid sodium salt (8.1 g, 35 mmol) in 9 M HCl (140 mL) was heated to 90° C. Crotonaldehyde (9.00 mL, 108 mmol), was then added over a 1.5 h period and the resultant mixture was allowed to stir overnight. The reaction mixture was allowed to cool for 10 min and the solid obtained was collected by filtration while warm. The solids formed from the filtrate upon further cooling were collected by filtration. The filtrate was again stirred for 30 min and a third crop of solids was collected by filtration. The combined solids were washed with water and dried under reduced pressure to afford compound 73a. Mass spectrum (LCMS, ESI pos.) Calcd. For C13H9NO2: 188.1 (M+H). found 188.2.

後処理

  1. temperatureto cool for 10 min
  2. customthe solid obtained
  3. filtrationwas collected by filtration
  4. temperaturewhile warm
  5. customThe solids formed from the filtrate
  6. temperatureupon further cooling
  7. filtrationwere collected by filtration
  8. stirringThe filtrate was again stirred for 30 min
  9. filtrationa third crop of solids was collected by filtration
  10. washThe combined solids were washed with water
  11. customdried under reduced pressure

出典と根拠

ORDレコード
ord-9eb0e70913e8469798b11c1d6ebeab6b
出典データセット
uspto-grants-2015_11
特許番号
US09193736B2

反応ノート

読み込み中…