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-Eintrag

ord-6b4b555a84ab448196e7c8c5c24c1e44

Quelldatensatz

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06613804B2