Sodium Hydroxide → 4-amino-2-methyl-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one
Reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]1[C:12]2[C:13](=[O:17])[N:14]([CH3:16])[CH2:15][C:11]=2[CH:10]=[CH:9][N:8]=1.[OH-].[Na+]>Cl>[NH2:6][C:7]1[C:12]2[C:13](=[O:17])[N:14]([CH3:16])[CH2:15][C:11]=2[CH:10]=[CH:9][N:8]=1Participants
4
Procedure
A solution of 4-[(2,4-dimethoxybenzyl)amino]-2-methyl-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one (1.8 g, 5.7 mmol) in 37% HCl (7.0 mL) was stirred at rt for 16 hours. The reaction mixture was neutralized with NaOH and extracted with EtOAc (15 mL). The organic layer was washed with water (10 mL), washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to yield a red solid. The crude material was purified by silica gel chromatography on the combi-flash Rf system using DCM/MeOH (100:0→95:5) as eluent. The fractions containing product were combined and concentrated under reduced pressure to yield an orange solid, (319 mg, 34%). 1H NMR (DMSO-d6, 400 MHz): δ=2.99 (s, 3 H), 4.37 (s, 2 H), 6.54 (br. s., 2 H), 6.73 (d, J=5.05 Hz, 1 H), 8.04 (d, J=5.05 Hz, 1 H). MS (ES+): m/z 164.07 [MH+] (TOF, polar).