HCID 70563141, compound → HCID 70564562, compound

HRID 126920Notes

Reaction equation

HRID 126920 reaction equation
[CH2:1]([N:3]1[CH2:7][C@@H:6]([OH:8])[C@H:5]([N:9]([CH3:21])[C:10](=[O:20])[C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH2:4]1)[CH3:2].[H][H]>C(O)C.[Pt]=O>[NH2:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]([N:9]([C@H:5]2[C@H:6]([OH:8])[CH2:7][N:3]([CH2:1][CH3:2])[CH2:4]2)[CH3:21])=[O:20])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 70563141HCID 70563141, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70564562HCID 70564562, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A solution of 23 g (79 mmoles) of trans-N-(1-ethyl-4-hydroxy-3-pyrrolidinyl)-N-methyl-4-nitrobenzamide in 250 ml of absolute ethanol was treated with platinum oxide and shaken with hydrogen at ambient temperature in the Parr reduction apparatus for 3 hr. The mixture was filtered and the filtrate was concentrated to give 20.6 g (100%) of crude product. One-half of the residue was crystallized from acetone to give 8.5 g (82%) of white powder; m.p. 142°-145° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give 20.6 g (100%) of crude product
  4. customOne-half of the residue was crystallized from acetone

Sources & evidence

ORD record
ord-88b86e0f878c4ccebe4bdacd4fddfa6a
Source dataset
uspto-grants-1981_03
Patent number
US04254135

Reaction notes

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