HCID 13003361, compound → HCID 12790654, compound

HRID 1155278Notes

Reaction equation

HRID 1155278 reaction equation
[CH2:1]([N:3]([CH2:6][CH2:7][NH:8][C:9](=[O:22])[C:10]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[C:12]([CH3:19])[C:11]=1[O:20][CH3:21])[CH2:4][CH3:5])[CH3:2].[H][H]>[Pt]=O.CO>[CH2:1]([N:3]([CH2:6][CH2:7][NH:8][C:9](=[O:22])[C:10]1[CH:15]=[C:14]([NH2:16])[CH:13]=[C:12]([CH3:19])[C:11]=1[O:20][CH3:21])[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 13003361HCID 13003361, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12790654HCID 12790654, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A mixture of N-(diethylaminoethyl)-2-methoxy-3-methyl-5-nitrobenzamide (4.25 g), platinum oxide (425 mg) and methanol (85 ml) is shaken in a hydrogen stream. After absorption of hydrogen stops, the reaction mixture is filtered to remove the catalyst. The filtrate is concentrated under vacuum and the residue is chromatographed on a column of alumina, which is eluated with methylene chloride to methylene chloride-2% methanol. The eluate is concentrated under vacuum and the residue is washed with isopropyl ether to give N-(diethylaminoethyl)-5-amino-2-methoxy-3-methylbenzamide (2.38 g) as crystals melting at 56° to 57° C.

Workup

  1. customAfter absorption of hydrogen
  2. filtrationthe reaction mixture is filtered
  3. customto remove the catalyst
  4. concentrationThe filtrate is concentrated under vacuum
  5. customthe residue is chromatographed on a column of alumina, which
  6. concentrationThe eluate is concentrated under vacuum
  7. washthe residue is washed with isopropyl ether

Sources & evidence

ORD record
ord-a31ae353ebf14471977a86d4d4a4d6c9
Source dataset
uspto-grants-1981_11
Patent number
US04301159

Reaction notes

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