Hydroxyamine hydrochloride → HCID 9877758, compound
Reaction equation
[CH:1]([C:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]2[CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][CH2:16][C:4]=12)=O.Cl.[NH2:25]O>C(O)=O>[CH2:16]1[C:4]2=[C:3]([C:1]#[N:25])[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]2[CH2:12][CH2:13][NH:14][CH2:15]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of tert-butyl 11-formyl-1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indole-3-carboxylate in formic acid (1 mL) is treated with hydroxylamine hydrochloride (90 mg, 1.3 mmol) and heated to reflux. After 18 hrs, the reaction mixture is cooled to rt, quenched with 1M sodium hydroxide (15 mL), and extracted twice with ethyl acetate (20 mL). The combined organics are washed once with brine (20 mL), dried over MgSO4, filtered, and concentrated to give 224 mg of a crude solid. This material is purified by LC (230-400) silica gel eluting with 5% methanol/dichloromethane to afford 123 mg of 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carbonitrile as a red solid, mp 161-164° C. IR (drift) 3313, 2935, 2906, 2203, 1539, 1463, 1421, 1351, 1328, 1272, 1208, 1185, 822, 769, 752 cm−1.