7-Hydroxychromanone → Methyl 3-(4-amino-2-methylphenyl)propanoate

HRID 1620030Notes

Reaction equation

HRID 1620030 reaction equation
OC1C=C2C(CCC(=O)O2)=CC=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]([O:24][CH3:25])=[O:23])=[C:16]([CH3:26])[CH:15]=1>[OH-].[Pd+2].[OH-]>[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[C:16]([CH3:26])[CH:15]=1

Participants

4

Reactant 2

HCID 2981307-HydroxychromanoneHCID 12433288HCID 12433288, compound

Product 1

HCID 54187007Methyl 3-(4-amino-2-methylphenyl)propanoateYield 74.2%

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

A reaction was performed according to the synthesis method of Intermediate 1 by using Intermediate 7 (2.0 g) and 10% palladium hydroxide/activated carbon (1.5 g). The reaction mixture was filtered through Celite, and the solvent of the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (Yamazen, n-hexane:ethyl acetate=3:1), and the solvent was evaporated under reduced pressure by using a rotary evaporator to obtain the title compound (1.5 g) (the reaction was performed in THF solvent (20 ml) for 20 hours).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent of the filtrate was evaporated under reduced pressure
  3. customThe residue was purified by column chromatography (Yamazen, n-hexane:ethyl acetate=3:1)
  4. customthe solvent was evaporated under reduced pressure
  5. customa rotary evaporator

Sources & evidence

ORD record
ord-0940bbcdb5ef4415ab4645c2ddf46bb5
Source dataset
uspto-grants-2014_07
Patent number
US08772327B2

Reaction notes

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