Tin tetrachloride → 4-Ethylbenzene-1,2-diamine

HRID 2182397Notes

Reaction equation

HRID 2182397 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([N+:10]([O-])=O)=[C:7]([CH:9]=1)[NH2:8])[CH3:2].[Sn](Cl)(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>C(O)C>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([NH2:10])=[C:7]([NH2:8])[CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 224779685-Ethyl-2-nitrobenzenamine

Product 1

HCID 123732134-Ethylbenzene-1,2-diamineYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 5-ethyl-2-nitro-aniline [200 mg, Reference Example 30(a)] and tin chloride (2.75 g) in ethanol (5 ml) was heated in a Smith Creator microwave at 140° C. for 10 minutes. The reaction mixture was basified to pH 8 by addition of saturated sodium hydrogen carbonate solution and then extracted with ethyl acetate. The organic extracts were dried over magnesium sulfate and then evaporated to give 4-ethyl-phenylene diamine (140 mg) as a pale orange solid, which was used without future purification. MS: 137.2 (M+H)+. HPLC (METHOD H): RT=2.91 minutes. (b) 4-Methoxy-5-methyl-benzene-1,2-diamine

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts were dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-b3d41f793bd042a9bb50f38a513121fa
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

Loading…