Anthranilic Acid → 2-Phenylquinoline-8-carboxylic acid

HRID 1199940Notes

Reaction equation

HRID 1199940 reaction equation
OS(O)(=O)=O.[C:6]([OH:15])(=[O:14])[C:7]1[C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH2:9].[N+]([C:19]1[CH:28]=[CH:27][C:22]([CH:23]=[CH:24][CH:25]=O)=[CH:21][CH:20]=1)([O-])=O.[OH-].[K+]>CC(O)=O.O>[C:22]1([C:23]2[CH:24]=[CH:25][C:10]3[C:8](=[C:7]([C:6]([OH:15])=[O:14])[CH:13]=[CH:12][CH:11]=3)[N:9]=2)[CH:27]=[CH:28][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 227Anthranilic AcidHCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 156143-(4-Nitrophenyl)prop-2-enal

Product 1

HCID 140689932-Phenylquinoline-8-carboxylic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of conc. H2SO4 (45 mL), water (5 mL), AcOH (5 mL), anthranilic acid (XI; R2 =H) (20.5 g) and H3AsO4 (80% w/w; 32 g) was heated with stirring to 105° C., and then treated with cinnamaldehyde (VIII; R1 =H) (25 g) at the rate which maintained the temperature at 105°-110° C. The reaction mixture was stirred for a further 3 h at 110°-115° C., then cooled and strongly basified with aqueous KOH. The aqueous layer was decanted from a quantity of tar, washed with CHCl3 and then acidified with AcOH. The resulting precipitate was chromatographed on SiO2 and eluted with a gradient of MeOH in CH2Cl2 to give a low yield of the desired acid, mp 160°-161° C., identical in all respects to the compound obtained in Example A. This compound was elaborated to compound 1 of Table I by the method outlined in Example A.

Workup

  1. temperaturewas heated
  2. temperaturemaintained the temperature at 105°-110° C
  3. stirringThe reaction mixture was stirred for a further 3 h at 110°-115° C.
  4. temperaturecooled
  5. customThe aqueous layer was decanted from a quantity of tar
  6. washwashed with CHCl3
  7. customThe resulting precipitate was chromatographed on SiO2
  8. washeluted with a gradient of MeOH in CH2Cl2

Sources & evidence

ORD record
ord-e72a61d6960941fba630fd021a63a3f5
Source dataset
uspto-grants-1990_02
Patent number
US04904659

Reaction notes

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