Hydrochloric Acid → HCID 9834916, compound
Reaction equation
[N+:1](/[CH:4]=[CH:5]/[C:6]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]2[CH2:15][CH2:16][N:17](C(OC(C)(C)C)=O)[CH2:18][CH2:19][C:7]=12)([O-:3])=[O:2].Cl>CO>[N+:1](/[CH:4]=[CH:5]/[C:6]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19][C:7]=12)([O-:3])=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of tert-butyl 11-[(E)-2-nitroethenyl]-1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indole-3-carboxylate (396 mg, 1.1 mmol) in methanol (10 mL) is cooled to 0° C. and treated with a saturated solution of hydrochloric acid in methanol (5 mL). After 3 hrs, the volatiles are removed under reduced pressure, diluted with 5M sodium hydroxide (15 mL), and extracted twice with dichloromethane (20 mL). The combined organics are washed once with brine (15 mL), dried over MgSO4, filtered, and concentrated to give a yellow solid. This material is recrystallized from dichloromethane/ethyl acetate to afford 209 mg of 11-[(E)-2-nitroethenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole as a light yellow solid, mp 225-226° C. IR (drift) 1603, 1488, 1469, 1318, 1301, 1281, 1257, 1251, 1206, 1187, 1062, 976, 946, 763, 745 cm−1; OAMS supporting ions at: ESI+ 258.1.