2-amino-5-iodo-3-methylbenzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of freshly prepared ethyl glycinate (2.58 g), 2-amino-5-iodo-3-methylbenzaldehyde (4.03 g) and 3Å molecular sieves (2 g "Fluka A.G." [Trade Mark] article No. 69828) was heated with stirring under reflux in chloroform (50 cm3) for 4 hours. The cooled solution was filtered, evaporated in vacuo, and the residue taken into ethanol (30 cm3) and treated with sodium cyanoborohydride (1.43 g). After stirring for 72 hours ethanol was removed in vacuo and the residue was partitioned between chloroform (50 cm3) and aqueous ammonia (50 cm3, S.G. 0.88). The aqueous phase was further extracted with chloroform (2×100 cm3) and the combined organic extracts were dried (MgSO4) and evaporated to give the title compound as a crude oil, (2.5 g). 69828) was heated The cooled solution was filtered evaporated in vacuo treated with sodium cyanoborohydride (1.43 g) After stirring for 72 hours ethanol was removed in vacuo the residue was partitioned between chloroform (50 cm3) and aqueous ammonia (50 cm3, S.G. 0.88) The aqueous phase was further extracted with chloroform (2×100 cm3) the combined organic extracts were dried (MgSO4) evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Freshly dried manganese dioxide (3.3 g) was added to a solution of 2-amino-5-iodo-3-methylbenzyl alcohol (2.0 g) in dichloromethane (50 cm3) under nitrogen and the mixture was stirred for 3 days at room temperature. The mixture was filtered, the filtrate evaporated to dryness, and the solid residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with dichloromethane. Combination and evaporation of appropriate fractions afforded the title compound, m.p. 134° (1.6 g). The mixture was filtered the filtrate evaporated to dryness the solid residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with dichloromethane Combination and evaporation of appropriate fractions

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Freshly dried manganese dioxide (3.3 g) was added to a solution of 2-amino-5-iodo-3-methylbenzyl alcohol (2.0 g) in dichloromethane (50 cm3) under nitrogen and the mixture was stirred for 3 days at room temperature. The mixture was filtered, the filtrate evaporated to dryness, and the solid residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with dichloromethane. Combination and evaporation of appropriate fractions afforded the title compound, m.p. 134° (1.6 g). The mixture was filtered the filtrate evaporated to dryness the solid residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with dichloromethane Combination and evaporation of appropriate fractions