Hydrochloric Acid → 3-carboethoxy-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid

HRID 2419014Notes

Reaction equation

HRID 2419014 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl[C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][N:16]=1.Cl.[CH2:25](O)[CH3:26]>>[C:11]([C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:6])[N:16]3[CH:17]=[C:18]([C:19]([OH:21])=[O:20])[CH:22]=[CH:23][C:15]3=[N:1]2)=[CH:7][CH:8]=1)([O:13][CH2:25][CH3:26])=[O:12]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 792226-Chloronicotinic acidHCID 27248222-Aminoterephthalic acid

Product 1

HCID 203168403-carboethoxy-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid

Procedure

A mixture of 2.00g (11.1 mmol) of 2-aminoterephthalic acid, 1.73g (11.1 mmol) of 6-chloronicotinic acid, 2.5ml of conc. HCl and 25ml of ethanol was heated at reflux for 67 hours. The mixture was cooled and filtered to give 0.90g of solid, mp. 275°-324°. The crude material was recrystallized from 1-propanol and gave 0.40g of the mono-esterified product, mp. 283°-293° dec.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 67 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-93063648ed9140e9bc35bc3b418620f1
Source dataset
uspto-grants-1978_08
Patent number
US04104389

Reaction notes

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