Anthranilic Acid → 11-Oxo-11H-pyrido(2,1-b)quinazoline-8-carboxylic acid

HRID 258556Notes

Reaction equation

HRID 258556 reaction equation
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].Cl[C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][N:13]=1.Cl>C(O)C>[O:10]=[C:1]1[C:2]2[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:4]=[C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][N:13]12

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 313Hydrochloric AcidHCID 792226-Chloronicotinic acid

Product 1

HCID 19843911-Oxo-11H-pyrido(2,1-b)quinazoline-8-carboxylic acidYield 44.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reaction mixture containing 4.35g (31.8 mmol) of anthranilic acid, 5.00g (31.8 mmol) of 6-chloronicotinic acid, 3ml of conc. HCl and 80ml of ethanol was heated at reflux for 21 hours. The mixture was cooled and filtered to give 3.40g (38.9%) of the expected product, mp. 323° -325° dec. The analytical sample was obtained by recrystallization from methanol-ether, mp. 323° -325° dec.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 21 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-8d3df2ae831d47c9b887a350c9374a89
Source dataset
uspto-grants-1977_07
Patent number
US04033961

Reaction notes

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