Sodium Sulfide → HCID 597187, compound

HRID 440821Notes

Reaction equation

HRID 440821 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:8]=2[C:9]([O:11]C)=[O:10])=[CH:4][CH:3]=1.[NH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:33][C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)=[C:27]([CH:32]=1)[C:28]([O:30]C)=[O:29].[H][H].[Sn](Cl)(Cl)(Cl)Cl.[S-2].[Na+].[Na+]>Cl.CO.O.[Pd].CO>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:8]=2[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[NH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:33][C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)=[C:27]([CH:32]=1)[C:28]([OH:30])=[O:29]

Participants

11

Reactant 5

HCID 14804Sodium SulfideHCID 24287Tin tetrachlorideHCID 22404866HCID 22404866, compoundHCID 22404905HCID 22404905, compoundHCID 178418361HCID 178418361, compound

Product 2

HCID 597187HCID 597187, compoundHCID 22404882HCID 22404882, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A.1. Methyl 2-(4-chlorophenoxy)-5-nitro-benzoate is reduced to methyl 5-amino-2-(4-chlorophenoxy)-benzoate using palladium/charcoal as the catalyst with the aid of hydrogen in a solvent such as methanol. Alternatively, this reduction step is carried out using tin tetrachloride in aqueous hydrochloric acid or using sodium sulfide in methanol/water at in each case elevated temperature either with the aforementioned ester or the free 2-(4-chlorophenoxy)-5-nitrobenzoic acid to give 5-amino-2-(4-chlorophenoxy)-benzoic acid, which subsequently is converted into methyl 5-amino-2-(4-chlorophenoxy)-benzoate by heating in methanolic hydrochloric acid.

Sources & evidence

ORD record
ord-b8ce744d78f641e1b893972d31a6fb4f
Source dataset
uspto-grants-1996_05
Patent number
US05521160

Reaction notes

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