8-Hydroxy-5-methyl-7-nitro-1,2,3,4,4a,9a-hexahydro-9-fluorenone → 7-Amino-8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone

HRID 2051424Notes

Reaction equation

HRID 2051424 reaction equation
[OH:1][C:2]1[C:3]([N+:17]([O-])=O)=[CH:4][C:5]([CH3:16])=[C:6]2[C:14]=1[C:13](=[O:15])[CH:12]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11]1>[C].[Pd].C(O)C>[NH2:17][C:3]1[C:2]([OH:1])=[C:14]2[C:6]([CH:7]3[CH:12]([C:13]2=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8]3)=[C:5]([CH3:16])[CH:4]=1

Participants

4

Reactant 1

HCID 151572238-Hydroxy-5-methyl-7-nitro-1,2,3,4,4a,9a-hexahydro-9-fluorenone

Product 1

HCID 151572247-Amino-8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenoneYield 79.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To 200 ml of ethanol were added 5.0 g of 8-hydroxy-5-methyl-7-nitro-1,2,3,4,4a,9a-hexahydro-9-fluorenone and 1 g of 5% palladium carbon and catalytic reduction was carried out at room temperature and under normal pressure. The catalyst was removed by filtration and the filtrate was concentrated to obtain 3.5 g of 7-amino-8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone (yellow crystal).

Workup

  1. customwas carried out at room temperature and under normal pressure
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a1defe20e00a41f9af7b6cf2a712141c
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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