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Sodium Hydroxide → 9-Amino-N11-ethyl-N6-methyl-6,11-dihydro-5H-pyrido(2,3-b)(1,5)benzodiazepin-5-one

HRID 1898881
Notes
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Reaction equation

HRID 1898881 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]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 44701211-Ethyl-6-methyl-9-nitropyrido(3,2-C)(1,5)benzodiazepin-5-oneHCID 516892Sodium Bicarbonate

Product 1

HCID 4532829-Amino-N11-ethyl-N6-methyl-6,11-dihydro-5H-pyrido(2,3-b)(1,5)benzodiazepin-5-oneYield 44.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

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

  1. extractionThe aqueous phase was then extracted with ethyl acetate
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe solid material obtained
  6. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fe2c4575845149408e5dd51e3bbd73e2
Source dataset
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05571809

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes