Water → HCID 10398135, compound

HRID 374439Notes

Reaction equation

HRID 374439 reaction equation
[N+]([O:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]2[CH:14]=[C:15]([N+:18]([O-])=O)[CH:16]=[CH:17][C:10]=2[O:9][CH2:8]1)([O-])=O.[H][H].O>CO.[Pd]>[NH2:18][C:15]1[CH:16]=[CH:17][C:10]2[O:9][CH2:8][N:7]([CH2:6][CH2:5][OH:4])[C:12](=[O:13])[C:11]=2[CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10379071SINITRODIL,6-NITROHCID 178418361HCID 178418361, compound

Product 1

HCID 10398135HCID 10398135, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 42 g (0.148 mole) of the compound of Example 1 in 6,300 ml of methanol was combined with 10% Pd/C, and the resulting mixture was placed in a hydrogen atmosphere having a head of water, at room temperature. At the end of the reaction, the suspension was filtered on celite and the solution obtained was evaporated under vacuum. The resulting crude product was taken up with ethyl ether and filtered under vacuum, thus yielding 30 g of 6-amino-2,3-dihydro-3-(2'-hydroxyethyl)-4H-1,3-benzoxazin-4-one. m.p. 94°-96° C. (ethyl ether).

Workup

  1. customat room temperature
  2. customAt the end of the reaction
  3. filtrationthe suspension was filtered on celite
  4. customthe solution obtained
  5. customwas evaporated under vacuum
  6. filtrationfiltered under vacuum

Sources & evidence

ORD record
ord-3101b70542154e1f9ddde6a568df6756
Source dataset
uspto-grants-1996_01
Patent number
US05480882

Reaction notes

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