Stannous chloride dihydrate → 4-Amino-2-ethoxybenzonitrile
Reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])[CH3:2].O.O.[Sn](Cl)Cl.C(=O)([O-])O.[Na+]>C(O)C>[NH2:12][C:10]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:3][CH2:1][CH3:2])[CH:11]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a suspension of 2-ethoxy-4-nitro-benzonitrile (0.49 g, 2.54 mmol) in ethanol (50 ml) is added tin (II) chloride dihydrate (2.87 g, 12.7 mmol) and the suspension is stirred at 70° C. for 2 hours and at room temperature overnight. The reaction mixture is poured onto ice-water and the pH of the solution is adjusted to pH 7-8 by addition of sodium hydrogen carbonate solution (5% solution in water). The aqueous emulsion is filtered under vacuum and the product is extracted with ethyl acetate (2×150 ml). The organic portions are combined, washed with brine (100 ml), dried (MgSO4) and concentrated in vacuo to yield the titled product as a pale yellow solid which is used in the next step without further purification.
Workup
- additionThe reaction mixture is poured onto ice-water
- filtrationThe aqueous emulsion is filtered under vacuum
- extractionthe product is extracted with ethyl acetate (2×150 ml)
- washwashed with brine (100 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c503b2d38a1c4c14b6eefc2ac56945bb
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08470848B2
Reaction notes
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