Ammonia → HCID 67199968, compound

Participants

Reaction Steps

To a solution of A4 (1.237 g, 3.76 mmol), in MeOH (50 mL) was added 38% aqueous formaldehyde (8.4 mL, 112.8 mmol, 30 eq), NaBH3CN (2.134 g, 30.08 mmol, 8 eq), NaOAc (526 mg, 6.41 mmol) and 2 drops of c. HCl. The reaction mixture was stirred at 20° C. for 2 h, by this time TLC (SiO2/8% MeOH/DCM/aq NH3) and mass spectrum showed completion of the reaction. Then the reaction mixture was acidified with c. HCl, stirred for 1 h. at 20° C. After this time the reaction mixture was carefully neutralize with aqueous NH3. The MeOH was evaporated under reduced pressure and the aqueous residue was the stirred with aqueous NH3. The resulting precipitate was filtered washed with water to give essentially pure A5 (1.22 g, 91%); This was used without further purification; mp, (MeOH)>280° C.; 1H NMR [(CD3)2SO] δ 9.95 (s, 1H, NH), 8.85 (bs, 1H, NH), 8.18 (d, J=5.5 Hz, 1H, ArH), 7.72 (d, J=9.3 Hz, 1H, ArH), 7.65 (d, J=8.8 Hz, 2H, ArH), 7.41 (dd, J=9.3, 2.6 Hz, 1H, ArH), 7.29-7.26 (m, 3H, ArH), 6.67 (d, J=5.5 Hz, 1H, ArH), 3.06 [s, 6H, N(CH3)2], 2.06 (s, 3H, COCH3); APCl+ve 321.

Provenance & Evidence