3-chloro-4-[(dimethylamino)methyl]aniline

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using the procedure of Example 1, Compound 13a2 was used in place of Compound 1j3 and carried forward to prepare 4-amino-2-chloro-N,N-dimethyl-benzamide Compound 13a3. 1M LAH (3.53 mL, 3.53 mmol) was added dropwise to a solution of Compound 13a3 (700 mg, 3.53 mmol) in THF (10 mL). After 10 minutes, the reaction was cooled to 0° C. and quenched with water. The mixture was extracted from ethyl ether with 1N HCl. The aqueous layer was adjusted to pH 10 with NaOH and the product was extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated to give 3-chloro-4-dimethylaminomethyl-phenylamine Compound 13a (150 mg) as a viscous brown oil. MS 185 (MH+). quenched with water The mixture was extracted from ethyl ether with 1N HCl the product was extracted with EtOAc The combined organic layers were dried over MgSO4 concentrated