Methane → HCID 61506956, compound

HRID 1493642Notes

Reaction equation

HRID 1493642 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][C:4]=1[CH3:10].[C:11]([O:15][CH3:16])(=[O:14])[CH:12]=O.C>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][CH2:12][C:11]([O:15][CH3:16])=[O:14])=[CH:5][C:4]=1[CH3:10]

Participants

6

Reactant 3

HCID 297MethaneHCID 672973-Methyl-4-methoxybenzenamineHCID 70205Acetic acid, 2-oxo-, methyl ester

Product 1

HCID 61506956HCID 61506956, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-methoxy-3-methylaniline (5 g, 0.0364 mol), methyl glyoxylate (5.5 g, 0.0619 mol) and palladium over charcoal (3.7 g; 10%) in methanol (300 ml) was stirred under a hydrogen atmosphere for 1 hour. The suspension was filtered through hyflo and evaporated to give a yellow solid. This was triturated with ether at ~-78° C. and filtered to give the title compound as a pale yellow solid (3.8 g, 50%) m.p. 69°-71° C.

Workup

  1. filtrationThe suspension was filtered through hyflo
  2. customevaporated
  3. customto give a yellow solid
  4. customThis was triturated with ether at ~-78° C.
  5. filtrationfiltered

Sources & evidence

ORD record
ord-ca70e5d30bff4597a356adeb1e1ef2da
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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