HCID 18761413, compound → HCID 18761430, compound

Participants

Reaction Steps

Pd/C 10% (45 mg) was added to 2-(4-benzyloxy-2-nitrophenyl)ethyl chloride (132 mg, 0.453 mmol). The mixture was then suspended in freezer chilled THF (30 mL). The suspension was degassed and purged 3 times with hydrogen and reduced under atmospheric pressure at room temperature. After 3 h the solution was checked by TLC (10% MeOH/CHCl3) and the solution was filtered by suction over Celite. The filter residue was washed with more CH2Cl2, and the filtrate was concentrated under reduced pressure to give 2-(2-amino-4-hydroxyphenyl)ethyl chloride as a white solid (60.7 mg, 0.354 mmol, 78%). Mp 96-100° C.; TLC (10% MeOH/CHCl3) Rf=0.34; 1H-NMR (CDCl3 in 1 drop DMSO-d6, 500 MHz) 8.20 (br s, 1H), 6.85 (d, 8.0, 1H), 6.27 (dd, 2.5, 8.0, 1H), 6.26 (d, 2.5, 1H), 4.00 (br s, 2H), 3.66 (t, 8.5, 2H), 2.90 (t, 8.5, 2H); IR (neat) 3139, 3020, 2954, 1622, 1594, 1513, 1464, 1560, 1306, 1265, 1246, 1197, 1175, 1079, 1049, 973, 848, 793, 722, 596, 646; EI-MS m/z (relative intensity) 171 (M+, 28); isotope pattern of M+ and M++2 agrees with the presence of one chlorine atom. Accurate mass (EI-MS) for C8H10ClNO: calcd. 171.0451, obsd. 171.0444.

Provenance & Evidence