Sodium Hydroxide → 9-Amino-N11-ethyl-N6-methyl-6,11-dihydro-5H-pyrido(2,3-b)(1,5)benzodiazepin-5-one
Reaction equation
[CH2:1]([N:3]1[C:9]2[CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=[CH:13][C:8]=2[N:7]([CH3:17])[C:6](=[O:18])[C:5]2[CH:19]=[CH:20][CH:21]=[N:22][C:4]1=2)[CH3:2].O.O.Cl[Sn]Cl.C(=O)(O)[O-].[Na+].[OH-].[Na+]>C(O)(=O)C.Cl>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]2[N:7]([CH3:17])[C:6](=[O:18])[C:5]3[CH:19]=[CH:20][CH:21]=[N:22][C:4]=3[N:3]([CH2:1][CH3:2])[C:9]=2[CH:10]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 0.3 g (1 mmol) of 6,11-dihydro-11-ethyl-6-methyl-9-nitro-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one in acetic acid (5 ml) was added a solution of SnCl2.2H2O (1.7 g) in concentrated hydrochloric acid (2.2 ml). The mixture was stirred at room temperature for 6 hours, and then poured into a saturated sodium bicarbonate solution and made basic with aqueous sodium hydroxide. The aqueous phase was then extracted with ethyl acetate, dried (MgSO4), filtered and concentrated in vacuo. The solid material obtained was recrystallized from ethyl acetate to give 0.12 g (44% of theory) of 6,11-dihydro-9-amino-11-ethyl-6-methyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, m.p. 193°-195° C.
Workup
- extractionThe aqueous phase was then extracted with ethyl acetate
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe solid material obtained
- customwas recrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-fe2c4575845149408e5dd51e3bbd73e2
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05571809
Reaction notes
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