Stannous Chloride → 2-Isopropyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride

HRID 1350497Notes

Reaction equation

[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-])=O)=[C:8]([CH:11]=1)[C:9]#[N:10])([CH3:3])[CH3:2].[Sn](Cl)[Cl:23]>Cl.C(O)C>[ClH:23].[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:19]=[C:9]([NH2:10])[C:8]=2[CH:11]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 86 °C

Procedure

Combine 5-isopropyl-2-(2-nitro-phenylamino)-benzonitrile (4.54 g, 16.1 mmol) and tin (II) chloride (10.92 g, 48.4 mmol) in 65.0 mL of 5N HCl solution and 65.0 mL of ethanol. Heat this mixture at 86° C. for 18 hours. Chilling the mixture precipitates the title compound as 4.22 g of a yellow solid: mp>250° C.; mass spectrum (ion spray): m/z=252 (M+1).

Workup

temperatureChilling the mixture
customprecipitates the title compound as 4.22 g of a yellow solid

Sources & evidence

ORD record: ord-71148e66e37d4e8986c84b02189aee28
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214673B2

Reaction notes

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