Potassium Iodide → 8-hydroxymethyl-2-isopropoxy-11H-pyrido[2,1-b]quinazoline-11-one benzoate

HRID 1702613Notes

Reaction equation

HRID 1702613 reaction equation
[CH:1]([O:4][C:5]1[CH:13]=[C:9]([C:10]([OH:12])=[O:11])[C:8]([NH2:14])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C([O:23][CH2:24][C:25]1[CH:26]=[N:27][C:28](Cl)=[CH:29][CH:30]=1)(=O)C1C=CC=CC=1.[I-].[K+].COCCOCCOCCOC>CO>[C:10]([OH:12])(=[O:11])[C:9]1[CH:13]=[CH:5][CH:6]=[CH:7][CH:8]=1.[OH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]2[N:27]([CH:26]=1)[C:10](=[O:12])[C:9]1[C:8](=[CH:7][CH:6]=[C:5]([O:4][CH:1]([CH3:2])[CH3:3])[CH:13]=1)[N:14]=2

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8189TriglymeHCID 127191892-Amino-5-(propan-2-yloxy)benzoic acidHCID 130523116-Chloro-3-pyridinemethanol benzoate

Product 1

HCID 205256758-hydroxymethyl-2-isopropoxy-11H-pyrido[2,1-b]quinazoline-11-one benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 1.0 g. of 5-isopropoxyanthranilic acid, 1.1 g. of 6-chloro-3-pyridinemethanol benzoate and 0.01 g. of potassium iodide in 10 ml. of triglyme was heated to 150° overnight under a stream of argon. On cooling, the reaction mixture was dissolved in hot methanol, filtered and evaporated to an orange oil. Chromatographic separation and recrystallization from hexane-dichloromethane yielded 8-hydroxymethyl-2-isopropoxy-11H-pyrido[2,1-b]quinazoline-11-one benzoate, mp 123°-126°.

Workup

  1. additionA suspension of 1.0 g
  2. temperatureOn cooling
  3. filtrationfiltered
  4. customevaporated to an orange oil
  5. customChromatographic separation and recrystallization from hexane-dichloromethane

Sources & evidence

ORD record
ord-a4bcd6a5ff19416282d1ea179452c622
Source dataset
uspto-grants-1982_09
Patent number
US04348396

Reaction notes

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