4-Chloroquinazoline → 4-Quinazolinamine, N-[2-(2-naphthalenyl)ethyl]-

HRID 35840

Reaction equation

HRID 35840 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[CH2:22][CH2:23][NH2:24].[OH-].[NH4+].O>>[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[CH2:22][CH2:23][NH:24][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 788644-ChloroquinazolineHCID 37843782-(2-Naphthyl)ethyl-amineHCID 86589665Water ammonium hydroxide

Product 1

HCID 1641614-Quinazolinamine, N-[2-(2-naphthalenyl)ethyl]-Yield 26.7%

Procedure

A mixture of 1.0 g of 4-chloroquinazoline and 2.0 g of 2-(2-naphthyl)ethyl amine was heated under nitrogen to 165°-170° C. for one hour. The mixture was cooled and then 200 ml of a 50/50 mixture of ammonium hydroxide/water was added. The product was extracted into CH2Cl2, and the resulting solution was treated with charcoal and filtered. The solution was then concentrated to dryness, and the residue was recrystallized from a mixture of pentane and CH2Cl2 to give: 0.480 g of the title product. Yield: 26.7%. M.P. 172°-174° C.

Workup

  1. temperaturewas heated under nitrogen to 165°-170° C. for one hour
  2. temperatureThe mixture was cooled
  3. additionwas added
  4. extractionThe product was extracted into CH2Cl2
  5. additionthe resulting solution was treated with charcoal
  6. filtrationfiltered
  7. concentrationThe solution was then concentrated to dryness
  8. customthe residue was recrystallized from a mixture of pentane and CH2Cl2
  9. customto give

Sources & evidence

ORD record
ord-39812333389f4f1ba1923e4b17188cbd
Source dataset
uspto-grants-1995_05
Patent number
US05411963

Linked notes

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