N-(4-butyl-2-nitrophenyl)-2-(dimethylamino)acetamide → N-(2-amino-4-n-butylphenyl)-2-dimethylaminoacetamide

HRID 1415645Notes

Reaction equation

HRID 1415645 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:17])[CH2:13][N:14]([CH3:16])[CH3:15])=[C:7]([N+:18]([O-])=O)[CH:6]=1)[CH2:2][CH2:3][CH3:4].[H][H]>[Pt]=O.C(O)C>[NH2:18][C:7]1[CH:6]=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:10]=[CH:9][C:8]=1[NH:11][C:12](=[O:17])[CH2:13][N:14]([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 21482988N-(4-butyl-2-nitrophenyl)-2-(dimethylamino)acetamideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21482970N-(2-amino-4-n-butylphenyl)-2-dimethylaminoacetamideYield 74.7%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

N-(4-n-butyl-2-nitrophenyl)-2-dimethylaminoacetamide (36 g), prepared as described above, platinum oxide (0.2 g) and ethanol (100 ml) were shaken together in an atmosphere of hydrogen at laboratory temperature and atmospheric pressure until the uptake of hydrogen was complete; 8.2 litres were absorbed. The mixture was filtered and the ethanol evaporated off. The resultant solid was recrystallised from petroleum spirit (b.p. 60°-80° C.) to give N-(2-amino-4-n-butylphenyl)-2-dimethylaminoacetamide (24.0 g), m.p. 63°-66° C.

Workup

  1. custom8.2 litres were absorbed
  2. filtrationThe mixture was filtered
  3. customthe ethanol evaporated off
  4. customThe resultant solid was recrystallised from petroleum spirit (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-fb48f993c0a34ddf94d33727f3a403f5
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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