Stannous Chloride → 4-(2-amino-4-chlorophenoxy)-N,N-diethylbenzamide

Reaction equation

[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:19]=[CH:18][C:10]([C:11]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)=[C:4]([N+:22]([O-])=O)[CH:3]=1.Cl[Sn]Cl>>[NH2:22][C:4]1[CH:3]=[C:2]([Cl:1])[CH:21]=[CH:20][C:5]=1[O:6][C:7]1[CH:19]=[CH:18][C:10]([C:11]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1

Participants

Reactant 2

HCID 24479Stannous Chloride

HCID 511497004-(4-chloro-2-nitrophenoxy)-N,N-diethylbenzamide

Product 1

HCID 684606784-(2-amino-4-chlorophenoxy)-N,N-diethylbenzamideYield 85%

Procedure

The product from Example 129a (1.0 g, 2.87 mmol) was reduced with SnCl2 following the procedure from Example 1f giving the title compound as a clear oil (772 mg, 85%).

Sources & evidence

ORD record: ord-e8ebb659614e4f7b8c7607274550d191
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338605B2

Reaction notes

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