Potassium Hydroxide → HCID 10199071, compound

HRID 1106452Notes

Reaction equation

HRID 1106452 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[N:9]([CH:10]=1)[C:8](=[O:11])[C:7]1[C:12]([OH:20])=[C:13]([CH2:17][CH2:18][CH3:19])[C:14]([OH:16])=[CH:15][C:6]=1[O:5]2.[OH-].[K+]>CO.C(OCC)(=O)C.[Ni]>[OH:16][C:14]1[C:13]([CH2:17][CH2:18][CH3:19])=[C:12]([OH:20])[C:7]2[C:8](=[O:11])[N:9]3[CH:10]=[CH:2][CH:3]=[C:4]3[O:5][C:6]=2[CH:15]=1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 9796118HCID 9796118, compound

Product 1

HCID 10199071HCID 10199071, compoundYield 36.4%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 60 mg (0.18 mmol) of 2-chloro-6,8-dihydroxy-7-propyl-9H-pyrrolo [2,1-b][1,3]benzoxazin-9-one in 4 mL of methanol was subjected to hydrogenation with 0.1 g Ra-Ni, 0.4 mL of 0.5N KOH in methanol, and H2 at 20 psi. The mixture was diluted with ethyl acetate and extracted with 1N HCl. The organic layer was dried (Na2SO4), concentrated, and the residue purified by preparative TLC (Silica Gel: CH2C2) to give 17 mg of the title compound: mp 170-171° C.

Workup

  1. extractionextracted with 1N HCl
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customthe residue purified by preparative TLC (Silica Gel: CH2C2)

Sources & evidence

ORD record
ord-8e962ddf37c24db794a850560863ed60
Source dataset
uspto-grants-2000_05
Patent number
US06057315

Reaction notes

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