HCID 8901300, compound → HCID 21483014, compound

HRID 1415641Notes

Reaction equation

HRID 1415641 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:22])[CH2:12][N:13]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:14])([O-])=O.[H][H]>CO.[Pt]=O>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:22])[CH2:12][N:13]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH3:14]

Participants

5

Reactant 2

HCID 8901300HCID 8901300, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21483014HCID 21483014, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A suspension of N-(2-nitrophenyl)-2-(N-benzyl-N-methylamino)acetamide (30 g) and platinum oxide (0.3 g) in methanol (500 ml) was shaken in an atmosphere of hydrogen at laboratory temperature and atmospheric pressure until the uptake of hydrogen was complete. 6.6 Litres of hydrogen were absorbed. The mixture was filtered, and evaporated to dryness to give an oil which was extracted with boiling cyclohexane (1litre). On cooling, N-(2-aminophenyl)-2-(N-benzyl-N-methylamino)acetamide (12.5 g) was obtained as off-white crystals, m.p. 75°-77° C.

Workup

  1. custom6.6 Litres of hydrogen were absorbed
  2. filtrationThe mixture was filtered
  3. customevaporated to dryness
  4. customto give an oil which
  5. extractionwas extracted with boiling cyclohexane (1litre)
  6. temperatureOn cooling

Sources & evidence

ORD record
ord-3438aba0faa643d19e43a91eef1d6002
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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