Stannous Chloride → 4-(2-amino-4-chlorophenoxy)-N-propylbenzamide

Reaction equation

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

Participants

Reactant 2

HCID 24479Stannous Chloride

HCID 259341484-(4-chloro-2-nitrophenoxy)-N-propylbenzamide

Product 1

HCID 684596204-(2-amino-4-chlorophenoxy)-N-propylbenzamideYield 92%

Procedure

The product from Example 127a (1.0 g, 2.99 mmol) was reduced with SnCl2 following the procedure from Example 1f giving the title compound as a clear oil (834 mg, 92%).

Sources & evidence

ORD record: ord-0c655460411c4f6583f1e816757fa01b
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338605B2

Reaction notes

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