Stannous Chloride → 4-(2-amino-4-chlorophenoxy)-N-methoxy-N-methylbenzamide

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]([N:13]([O:15][CH3:16])[CH3:14])=[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]([N:13]([O:15][CH3:16])[CH3:14])=[O:12])=[CH:9][CH:8]=1

Participants

Reactant 2

HCID 24479Stannous Chloride

HCID 787761354-(4-chloro-2-nitrophenoxy)-N-methoxy-N-methylbenzamide

Product 1

HCID 866154954-(2-amino-4-chlorophenoxy)-N-methoxy-N-methylbenzamideYield 100%

Procedure

The product from Example 128a (1.0 g, 2.97 mmol) was reduced with SnCl2 following the procedure from Example 1f giving the title compound as a clear oil (911 mg, 100%).

Sources & evidence

ORD record: ord-28b3e7bcb4b34022b1f9a7439f196474
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338605B2

Reaction notes

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