7-benzyloxy-3,4-dihydro-2H-2,4a,5-triaza-fluoren-1-one → 7-hydroxy-3,4-dihydro-2H-2,4a,5-triaza-fluoren-1-one

HRID 2105426Notes

Reaction equation

HRID 2105426 reaction equation
C([O:8][C:9]1[CH:21]=[C:20]2[C:12]([N:13]3[C:18](=[CH:19]2)[C:17](=[O:22])[NH:16][CH2:15][CH2:14]3)=[N:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(O)=O>[OH:8][C:9]1[CH:21]=[C:20]2[C:12]([N:13]3[C:18](=[CH:19]2)[C:17](=[O:22])[NH:16][CH2:15][CH2:14]3)=[N:11][CH:10]=1

Participants

4

Reactant 1

HCID 684655717-benzyloxy-3,4-dihydro-2H-2,4a,5-triaza-fluoren-1-one

Product 1

HCID 684640317-hydroxy-3,4-dihydro-2H-2,4a,5-triaza-fluoren-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 284Formic AcidSolvent

Procedure

The suspension consistent of 0.20 g (0.68 mmol) 7-benzyloxy-3,4-dihydro-2H-2,4a,5-triaza-fluoren-1-one and 30 μg palladium on activated charcoal (10% Pd; commercially available) in 2 mL formic acid was hydrogenated at room temperature at 1.5 bar for 3 hours. The reaction mixture was filtered over dicalite speed plus® (Aldrich), the filter cake was washed with formic acid and the volatile components were evaporated at a rotary evaporator. The residue was stirred in 3 mL ethyl acetate, filtered and the light brown product (65%) was dried under high vacuum.

Workup

  1. filtrationThe reaction mixture was filtered over dicalite speed plus® (Aldrich)
  2. washthe filter cake was washed with formic acid
  3. customthe volatile components were evaporated at a rotary evaporator
  4. filtrationfiltered
  5. dry with materialthe light brown product (65%) was dried under high vacuum

Sources & evidence

ORD record
ord-a88524aed3304fdc848487d91ba1edc6
Source dataset
uspto-grants-2009_08
Patent number
US07579351B2

Reaction notes

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