Diisopropylethylamine → HCID 86689289, compound

Participants

Reaction Steps

A 1 L 3-neck flask fitted with a stir-bar, addition funnel, and an Ar inlet was charged with 4-amino-3-nitrophenol (10.1 g, 65.6 mmol) and CH2Cl2 (250 mL). To the resultant suspension cooled in an ice bath, was added iPr2NEt (33.8 g, 45.6 mL, 262 mmol) forming a deep red solution. Acid chloride 47a (32.4 g, 151 mmol) in CH2Cl2 (250 mL) was then added over 30 min. The mixture stirred overnight at rt. Saturated NaHCO3 (300 mL) was added, and the organic phase was washed with saturated NaHCO3 (300 mL) and brine (200 mL). The solution was filtered through phase separation paper and concentrated in vacuo to 36 g of a yellow-brown solid. The solid was triturated with EtOAc:hexanes 1:1 (150 mL), filtered, pressed with rubber dam, and rinsed with EtOAc:hexanes 1:1 (2×25 mL). The material dried to give 19.4 g of 62b as a yellow solid (58%). 1H NMR (300 MHz, CDCl3): δ 11.58 (s, 1H), 8.99 (d, 1H), 8.08 (d, 1H), 7.49 (dd, 1H), 7.33-7.18 (m, 2H), 6.71-6.48 (m, 6H), 4.89 (s, 2H), 4.66 (s, 2H), 4.06 (qt, 2H), 4.03 (qt, 2H), 1.43 (t, 3H), 1.42 (t, 3H) ppm. HPLC analysis (10:10:80 H2O:A1:MeOH) showed a purity of 93% with a retention time of 11.0 min.

Provenance & Evidence