Réaction #2465

Équation de réaction

ammonia

acetate

( ii )

1-(2-acetoxypropionyl)-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline

H2SO4

→

desired product

Rendement 75.0%

4-amino-1,1,3-trimethylindane

Rendement 75.0%

Solvants

—

Petrol

acetic acid

water

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas cautiously added dropwise
2. 2
   Températurethe mixture heated at 100° C. for 3 hours
3. 3
   AutreSeparation of the organic layer
4. 4
   Séchagedrying (MgSO4) and solvent flash

Mode opératoire

The acetate compound prepared in B (ii) (55 g, GC purity 91%, 0.172 moles) was added over 45 minutes to 98% H2SO4 (50 ml) at 25°-60° C. (exotherm). After stirring for a further 30 minutes at 60° C., water (50 ml) containing acetic acid (10 ml) was cautiously added dropwise and the mixture heated at 100° C. for 3 hours. Petrol (60/80 b.p., 100 ml) was added and the mixture basified to pH 9 with 35% aqueous ammonia (150 ml). Separation of the organic layer, drying (MgSO4) and solvent flash gave the desired product (22.6 g, GC purity 92%, yield 69%). NMR analysis using chiral solvating agent [(-)-2,2,2-trifluoro-1-(9-anthryl)ethanol] showed a 70/30 mixture of enantiomers in favour of the (-)-isomer.

Source