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(2-(tert-butyl)-5-chlorophenyl)hydrazine trifluoroacetic acid salt[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
18%
To a solution of <strong>[25414-78-2]2-(tert-butyl)-5-chloroaniline</strong> (0.500 g, 2.72 mmol) in acetic acid (1.5 mL, 26.2 mmol) at rt was added concentrated hydrochloric acid (2.4 mL, 79.0 mmol) in one portion. To the resulting mixture at -10 to -5 oC was added a solution of sodium nitrite (0.225 g, 3.27 mmol) in water (0.7 mL) over 10 min. The mixture was stirred at -5 to 0 oC for 45 min before a solution of tin(II) chloride dihydrate (1.136 g, 5.99 mmol) in concentrated hydrochloric acid (2.4 mL, 79.0 mmol), pre-cooled at 0 oC, was added over 10 min. The mixture was stirred at -10 to 0 oC for 1 h. The precipitating product, was collected as a pale solid by suction filtration and dried under vacuum. This product was purified by preparative HPLC (Column: Sunfire C18 OBD, 30 x 100 mm, 5-mum particles; Mobile Phase A: 5:95 acetonitrile: water with 0.1% TFA; Mobile Phase B: 95:5 acetonitrile: water with 0.1% TFA; Gradient: 10-100% B over 10 minutes, then a 5- minute hold at 100% B; Flow: 40 mL/min) to afford (2-(tert-butyl)-5- chlorophenyl)hydrazine TFA (150 mg, 18 % yield) as beige solid: MS (ESI) m/z: 199.3 [M+H]+; 1H NMR (400 MHz, Methanol-d4) delta 7.42 (d, J = 8.5 Hz, 1H), 7.15 (d, J = 2.1 Hz, 1H), 7.12 (dd, J = 8.4, 2.2 Hz, 1H), 1.45 (s, 9H).
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