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

HRID 718689Notes

Reaction equation

HRID 718689 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 3199762-Methyl-5-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9eb0e70913e8469798b11c1d6ebeab6b
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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