HCID 14207564, compound → HCID 14207565, compound

HRID 1252735Notes

Reaction equation

HRID 1252735 reaction equation
[CH3:1][C:2]1[C:7]2[C:8](=[O:16])[O:9][C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[N:11][C:6]=2[CH:5]=[C:4]([O:17]CC2C=CC=CC=2)[CH:3]=1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][C:2]1[C:7]2[C:8](=[O:16])[O:9][C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[N:11][C:6]=2[CH:5]=[C:4]([OH:17])[CH:3]=1

Participants

5

Reactant 2

HCID 14207564HCID 14207564, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14207565HCID 14207565, compoundYield 63.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-methyl-7-benzyloxy-2-isopropoxy-4H-3,1-benzoxazin-4-one (50 mg) in ethyl acetate (80 ml) was hydrogenated over 10% palladium on charcoal at 50 psi hydrogen on a Parr hydrogenator for 5 hours. The catalyst was removed by suction filtration through Celite. The filtrate was evaporated to give a white solid which was further purified by thick layer chromatography (30% ethyl acetate: pet. ether 30-60) to give 5-methyl-7-hydroxy-2-isopropoxy-4H-3,1-benzoxazin-4-one as a white solid (23 mg), m.p. 258°-260° C. (decomp.), IR (KBr): 3100-3400, 1715, 1650, 1600 cm-1. H--NMR (CDCl3): 1.40 (d, 6H, CH3CHCH3), 2.40 (s, 3H, CH3), 5.3 (p, 1H, CH), 6.7 (m, 2H, ArH).

Workup

  1. customThe catalyst was removed by suction filtration through Celite
  2. customThe filtrate was evaporated
  3. customto give a white solid which
  4. customwas further purified by thick layer chromatography (30% ethyl acetate: pet. ether 30-60)

Sources & evidence

ORD record
ord-190e8a76a9304cd4adfa567594e0eeb0
Source dataset
uspto-grants-1988_05
Patent number
US04745116

Reaction notes

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