HCID 15372521, compound → HCID 15372522, compound

HRID 1289884Notes

Reaction equation

HRID 1289884 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:13]([C:14](=O)[CH:15]=1)=[CH:12][CH:11]=[C:10]([N+:17]([O-])=O)[C:9]=2[CH3:20])=[O:5])[CH3:2]>[Pd].C(O)(=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([CH3:20])[C:10]([NH2:17])=[CH:11][CH:12]=2)[O:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 15372521HCID 15372521, compound

Product 1

HCID 15372522HCID 15372522, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 8-methyl-7-nitro-4-oxo-4H-chromene-2-carboxylic acid ethyl ester (42.2 g, 0.152 mol) and palladium on carbon (4.7 g) in glacial acetic acid was hydrogenated at 50 psi for 48 hours. The catalyst was filtered through Celite® and the solvent removed under high vacuum. The crude product was chromatographed (25% ethyl acetate in hexanes) to afford 24.5 g (0.104 mol, 68.4%) of 7-amino-8-methyl-chroman-2-carboxylic acid ethyl ester as an orange oil which solidified upon standing: mp 82°-85°C.

Workup

  1. filtrationThe catalyst was filtered through Celite®
  2. customthe solvent removed under high vacuum
  3. customThe crude product was chromatographed (25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b47fd70c4c514773a0c11a45528a9528
Source dataset
uspto-grants-1998_05
Patent number
US05750556

Reaction notes

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