Aniline → HCID 22692581, compound

HRID 889102Notes

Reaction equation

HRID 889102 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:13][C:14]1C=CC=[CH:16][CH:15]=1.C(N(CC)CC)C.C(OC(=O)C)C>C(#N)C.CCCCCC>[Cl:1][C:2]1[N:11]=[C:10]([NH:13][CH2:14][CH2:15][CH3:16])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 2528862,4-Dichloroquinazoline

Product 1

HCID 22692581HCID 22692581, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Conditions

Temperature
60 °C

Procedure

2,4-Dichloroquinazoline (500 mg, 2.5 mmol) was dissolved in acetonitrile (3 mL). Aniline (260 mg, 2.76 mmol) and triethylamine (380 mg, 3.75 mmol) were added. The mixture was shaken in a sealed vial on a sand bath at 60° C. for 12 hours. Filtration and evaporation of the filtrate gave a yellow solid. Column chromatography (ethylacetate:hexane) gave (2-chloro-quinazolin-4-yl)-propylamine (350 mg, 55%).

Workup

  1. filtrationFiltration and evaporation of the filtrate
  2. customgave a yellow solid

Sources & evidence

ORD record
ord-4c9a5229d7764fa7b5b2f32c72365788
Source dataset
uspto-grants-2012_08
Patent number
US08252806B2

Reaction notes

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