2-Amino-5-chlorobenzamide → HCID 178517743, compound

Participants

Reaction Conditions

Reaction Steps

Preparation D8, Step 1: 2-Amino-5-chlorobenzamide (Avocado) (0.50 g, 2.93 mmol, 1 eq.), methyl 4-phenylbutyrate (3.14 g, 17.6 mmol, 6 eq.), NaOEt in ethanol (3.09 M, 5.69 mL, 17.6 mmol, 6 eq.) and ethanol (20 mL) were refluxed overnight. Cooled to 25° C. Added 10 mL of 10% HOAc/H2O. Solids formed which were filtered, the solids rinsed with 5 mL H2O, then dissolved in 20 mL of EtOAc/THF. Dried and stripped in vacuo followed by purification over silica gel in 3:1 to 1:1 Hexanes/EtOAc to give 6-chloro-2-(3-phenyl-propyl)-quinazolin-4-ol as a tan solid (200 mg). MS found: (M+H)+=299.

Provenance & Evidence