Pyridine → HCID 70576194, compound

HRID 1413811Notes

Reaction equation

HRID 1413811 reaction equation
N[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[C:13](Cl)(=[O:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[N:21]1C=CC=CC=1>O1CCOCC1>[C:13]([C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([NH2:21])[CH:3]=1)(=[O:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2337BenzocaineHCID 67340Hexanoyl chloride

Product 1

HCID 70576194HCID 70576194, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 4-amino-benzoate (8.5 g) dissolved in dioxane (50 ml) is reacted with hexanoyl chloride (7 g) and pyridine (7 ml) at the reflux temperature for one hour. After cooling and dilution with water, the product is extracted with ethylacetate and the organic layer is washed first with 1 N HCl and then with 5% NaHCO3. Evaporation to dryness yields ethyl 4-hexanoyl-amino-benzoate (10 g) which is dissolved in dry xilene (100 ml) and reacted with ethyl carbamate (6 g) and phosphorus pentoxide (35 g) for 5 hours at the reflux temperature. After cooling, pour in ice-water, neutralize with 2 N NaOH and separate the organic layer. Evaporation to dryness yields raw 6-carbethoxy-2-pentyl-3,4-dihydro-4-oxo-quinazoline (12.1 g) which is hydrolyzed with 2 N NaOH (30 ml) in dioxane (30 ml) for 16 hours at room temperature, to give 6-carboxy-2-pentyl-3,4-dihydro-4-oxo-quinazoline (7.9 g; m.p. 310°- 312° C., after crystallization from ethanol).

Workup

  1. temperatureAfter cooling
  2. extractiondilution with water, the product is extracted with ethylacetate
  3. washthe organic layer is washed first with 1 N HCl
  4. customEvaporation to dryness

Sources & evidence

ORD record
ord-0b75bbabee054b88a7b5814d2f7c451d
Source dataset
uspto-grants-1981_02
Patent number
US04251531

Reaction notes

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