Nitric Acid → 6-Methyl-1,3-dioxaindan-5-amine

To a solution of (3,4-methylenedioxy)toluene (5 ml) in acetic acid (20 ml) cooled with a cold water bath was added, dropwise, nitric acid (70%, 5 ml). The mixture was stirred for 45 min. To work up, water (100 ml) was added and the resulting yellow precipitate was filtered and washed with water until the aqueous filtrate was colorless. The yellow solid was dissolved in EtOAc (250 ml) and dried (MgSO4), and the solid was filtered off. The filtrate was subjected to catalytic hydrogenation (10% Pd/C, 1 atm) for 12 hours. The reaction mixture was then filtered off the catalyst and the filtrate was concentrated on a rotavap to give (3,4-methylenedioxy)-6-methylaniline as a brownish grey solid (5.49 g, 87% yield).

1. additionwas added
2. filtrationthe resulting yellow precipitate was filtered
3. washwashed with water until the aqueous filtrate
4. dissolutionThe yellow solid was dissolved in EtOAc (250 ml)
5. dry with materialdried (MgSO4)
6. filtrationthe solid was filtered off
7. waitThe filtrate was subjected to catalytic hydrogenation (10% Pd/C, 1 atm) for 12 hours
8. filtrationThe reaction mixture was then filtered off the catalyst
9. concentrationthe filtrate was concentrated on a rotavap

ORD record

ord-dc1439be9a6245c68fc8d99b97f98be7

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06331637B1