Stannous Chloride → 3-Allyloxycarbonyl-5-aminobenzamide

HRID 1824600Notes

Reaction equation

HRID 1824600 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([N+:16]([O-])=O)[CH:15]=1)[C:10]([NH2:12])=[O:11])=[O:6])[CH:2]=[CH2:3].Cl[Sn]Cl>>[CH2:1]([O:4][C:5]([C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([NH2:16])[CH:15]=1)[C:10]([NH2:12])=[O:11])=[O:6])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 24479Stannous ChlorideHCID 221685603-Allyloxycarbonyl-5-nitrobenzamide

Product 1

HCID 221686283-Allyloxycarbonyl-5-aminobenzamideYield 56.8%

Procedure

3-Allyloxycarbonyl-5-nitrobenzamide (1 g) was reduced with SnCl2 by a similar method to the reduction in example 12, giving 3-allyloxycarbonyl-5-aminobenzamide (0.5 g). Nmr (DMSO-d6): 4.78 (dt, 2H); 5.2-5.8 (broad, 2H); 5.26-5.45 (m, 2H); 5.91-6.13 (m, 1H); 7.22 (broad s, 1H); 7.27 (t, 1H); 7.33 (t, 1H); 7.59 (s, 1H).

Sources & evidence

ORD record
ord-baf749f27a0740ec96936443b589816c
Source dataset
uspto-grants-2006_05
Patent number
US07041836B2

Reaction notes

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