Sodium borohydride → HCID 14099539, compound

HRID 568747Notes

Reaction equation

HRID 568747 reaction equation
[CH2:1]([N:4]1[C:9]2[CH:10]=[C:11]([N:14]3[C:18](=[O:19])[C:17]([CH3:20])=[C:16]([CH3:21])[C:15]3=[O:22])[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][C:5]1=[O:23])[CH2:2][CH3:3].[BH4-].[Na+]>CO.C(O)(=O)C>[CH2:1]([N:4]1[C:9]2[CH:10]=[C:11]([N:14]3[C:15](=[O:22])[C:16]([CH3:21])=[C:17]([CH3:20])[CH:18]3[OH:19])[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][C:5]1=[O:23])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 14099186HCID 14099186, compound

Product 1

HCID 14099539HCID 14099539, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

1.15 g of 1-[4-propyl-2H-1,4-benzoxazin-3(4H)-on-6-yl]-3,4-dimethyl-2,5-dioxo-2,5-dihydropyrrole was dissolved in 100 ml of methanol, and 0.09 g of sodium borohydride was added at room temperature. The mixture was stirred at this temperature for 3 hours. One drop of acetic acid was added, and methanol was evaporated. The concentrated residue was extracted with dichloromethane, washed with water and dried. The solvent was evaporated, and the precipitated crystals were recrystallized with ethanol to give 0.8 g of 1-[4-propyl-2H-1,4-benzoxazin-3(4H)-on-6-yl]-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole. m.p. 124°-125° C.

Workup

  1. custommethanol was evaporated
  2. extractionThe concentrated residue was extracted with dichloromethane
  3. washwashed with water
  4. customdried
  5. customThe solvent was evaporated
  6. customthe precipitated crystals were recrystallized with ethanol

Sources & evidence

ORD record
ord-a19f98f662294ab3bcb191ce1fc87a26
Source dataset
uspto-grants-1988_03
Patent number
US04729784

Reaction notes

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