Hydrochloric Acid → 2-Methyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride

HRID 131313

Reaction equation

HRID 131313 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-])=O)=[C:6]([CH:9]=1)[C:7]#[N:8].O.O.[Sn](Cl)[Cl:23].Cl>C(O)C>[ClH:23].[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:17]=[C:7]([NH2:8])[C:6]=2[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 210935375-Methyl-2-(2-nitro-phenylamino)-benzonitrile

Product 1

HCID 210935072-Methyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochlorideYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 5-methyl-2-(2-nitro-phenylamino)-benzonitrile (4.03 g, 15.91 mmol), tin(II) chloride dihydrate (10.77 g, 47.74 mmol), 5N HCl (65 ml), and ethanol (40.0 ml) and stir the mixture at reflux. After 7 hours, cool to ambient temperature and chill in the refrigerator overnight. Remove the resulting precipitate by vacuum filtration and place the precipitate in ethanol (100.0 ml) and 5N HCl (20.0 ml) and heat at reflux for 19 hours. Cool the reaction mixture to ambient temperature and chill in the refrigerator. Filter off the resulting precipitate by vacuum filtration and dry it in a vacuum oven to give 2.59 g (63%) of an orange solid: mass spectrum (ion spray): m/z=224.0 (M+1).

Workup

  1. temperatureat reflux
  2. temperaturechill in the refrigerator overnight
  3. customRemove the resulting precipitate
  4. filtrationby vacuum filtration and place the precipitate in ethanol (100.0 ml)
  5. temperature5N HCl (20.0 ml) and heat
  6. temperatureat reflux for 19 hours
  7. temperatureCool the reaction mixture to ambient temperature
  8. temperaturechill in the refrigerator
  9. filtrationFilter off the resulting precipitate
  10. filtrationby vacuum filtration
  11. customdry it in a vacuum oven

Sources & evidence

ORD record
ord-fe8387ace88d451a8ad3c8ff0bc7c892
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Linked notes

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