Tetrahydrofuran → 2,4,5-Triamino-3-chloro-benzoic acid methyl ester

Participants

Reaction Steps

To a suspension of 4.4 g (16.19 mmol) of 4-amino-2-azido-3-chloro-5-nitro-benzoic acid methyl ester in 161 mL of a mixture EtOH:MeOH 2:1 (v/v), 161 mL of a saturated NH4Cl aqueous solution is added followed by the addition of 88 mL of THF. Then 5.2 g (81 mmol) of powdered zinc is added and the reaction is stirred at ambient temperature during 5 h. The suspension is diluted with CH2Cl2 and the organic phase is washed with brine (2 times) and then dried on Na2SO4. After filtration and evaporation 3.2 g (14.84 mmol, 92%) of a dark violet-red solid were obtained and used directly in the next step without more purification. LC/MS: 216/218 (M+1)+

Provenance & Evidence