2-nitro-9h-fluoren-1-ol → Fluoren-1-ol, 2-amino- (8CI)

HRID 1419402Notes

Reaction equation

HRID 1419402 reaction equation
[OH:1][C:2]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[N+:15]([O-])=O>CO.[Pd]>[NH2:15][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:13][C:14]=2[C:2]=1[OH:1]

Participants

4

Reactant 1

HCID 2425562-nitro-9h-fluoren-1-ol

Product 1

HCID 96452Fluoren-1-ol, 2-amino- (8CI)Yield 81.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-hydroxy-2-nitrofluorene(250 mg, 1.23 mmol) in methanol(250 mL) was added 10% Pd/C (1 g). The mixture was flushed with argon, then hydrogen was bubbled through the solution for 10 min. and a hydrogen atmosphere was maintained at balloon pressure overnight. The mixture was filtered through celite and the celite was washed with methanol. The solvent was evaporated and chromatography of the resulting solid on silica gel (5% MeOH/CH2Cl2) gave the desired product(171 mg, 81.2%). 1H NMR (CD3OD): δ 7.60 (d, 1H), 7.47 (d, 1H), 7.28 (t, 1H), 7.18 (m, 2H), 6.82 (d, 1H), 3.76 (s, 2H).

Workup

  1. customThe mixture was flushed with argon
  2. customhydrogen was bubbled through the solution for 10 min.
  3. temperaturea hydrogen atmosphere was maintained at balloon pressure overnight
  4. filtrationThe mixture was filtered through celite
  5. washthe celite was washed with methanol
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b2ca94e05de44739ba421a6b3f1d21b6
Source dataset
uspto-grants-1999_03
Patent number
US05886044

Reaction notes

Loading…