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

HRID 718689노트

반응식

HRID 718689 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 3199762-Methyl-5-quinolinecarboxylic acid

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9eb0e70913e8469798b11c1d6ebeab6b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193736B2

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