Hydrochloric Acid → 3-Methyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride

HRID 131314Notes

Reaction equation

HRID 131314 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-])=O)[CH:3]=1.O.O.[Sn](Cl)[Cl:23].Cl>C(O)C>[ClH:23].[CH3:1][C:2]1[CH:9]=[CH:8][C:5]2[C:6]([NH2:7])=[N:17][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[NH:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 210935294-Methyl-2-(2-nitro-phenylamino)-benzonitrile

Product 1

HCID 210935233-Methyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochlorideYield 49.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 4-methyl-2-(2-nitro-phenylamino)-benzonitrile (2.46 g, 9.71 mmol), tin(II) chloride dihydrate (6.57 g, 29.71 mmol), 5N HCl (40 ml), and ethanol (40.0 ml). and stir the mixture at reflux. After 8 hours, cool to ambient temperature. Allow the mixture to stand at ambient temperature overnight and chill for an additional 3 hours in the refrigerator. Remove the resulting precipitate by vacuum filtration and dry it under vacuum to give 1.24 g (49%) of the desired compound as a yellow solid: mass spectrum (ion spray): m/z=224.0 (M+1).

Workup

  1. temperatureat reflux
  2. waitAllow the mixture to stand at ambient temperature overnight
  3. temperaturechill for an additional 3 hours in the refrigerator
  4. customRemove the resulting precipitate
  5. filtrationby vacuum filtration
  6. customdry it under vacuum

Sources & evidence

ORD record
ord-8da5f4fe761246a5857de7c4fa801ff8
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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