Methanol → 3-Amino-1-(4-methoxyphenyl)but-2-en-1-one

HRID 638197Notes

Reaction equation

HRID 638197 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:14])[CH2:10][C:11](=O)[CH3:12])=[CH:5][CH:4]=1.[OH-:15].[NH4+:16].[CH3:17]O>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:14])[CH:10]=[C:11]([CH3:12])[NH2:16])=[CH:5][CH:4]=1.[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([CH:17]=[O:15])=[C:10]([CH3:11])[NH2:16])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 776401-(4-Methoxyphenyl)butane-1,3-dione

Product 2

HCID 15171633-Amino-1-(4-methoxyphenyl)but-2-en-1-oneHCID 867405674-Methoxyphenyl-1-methyl-3-oxo-1-propenamine

Procedure

The intermediate 3-(4-methoxyphenyl)-1-methyl-3-oxo-1-propenamine was prepared as follows: A mixture containing 106 g of 1-(4-methoxyphenyl)-1,3-butanedione, 500 ml of methanol and 200 ml of concentrated aqueous ammonium hydroxide was allowed to stand at room temperature for 4 hours and then chilled in a refrigerator. The separated crystalline product was collected, washed with ether and dried at 90°-95° C. to yield 93.7 g of 3-(4-methoxyphenyl-1-methyl-3-oxo-1-propenamine, m.p. 126°-128° C.

Workup

  1. temperaturechilled in a refrigerator
  2. customThe separated crystalline product was collected
  3. washwashed with ether
  4. customdried at 90°-95° C.

Sources & evidence

ORD record
ord-20a53e81f4a4421c83d3b5634084ecbb
Source dataset
uspto-grants-1985_12
Patent number
US04560691

Reaction notes

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