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

HRID 323081Notes

Reaction equation

HRID 323081 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): d 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-cbc7b2e307b94ee28d905e5ee59d6950
Source dataset
uspto-grants-2001_04
Patent number
US06211373B1

Reaction notes

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