HCID 23513713, compound → HCID 23513707, compound

HRID 1821448Notes

Reaction equation

HRID 1821448 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:26]=[CH:25][C:8]([C:9]([CH:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[N+:21]([O-])=O)[C:12]2=[O:24])=[O:10])=[CH:7][CH:6]=1>C1COCC1.[Pd]>[NH2:21][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:18]=1[C:19](=[O:20])[CH:11]([C:9](=[O:10])[C:8]1[CH:25]=[CH:26][C:5]([O:4][CH2:3][CH2:2][Cl:1])=[CH:6][CH:7]=1)[C:12]2=[O:24]

Participants

4

Reactant 1

HCID 23513713HCID 23513713, compound

Product 1

HCID 23513707HCID 23513707, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-[4-(2-chloroethoxy)benzoyl]-4-nitroindan-1,3-dione (27 g, 72 mmol) in THF (1200 mL) under argon was added 10% Pd/C (2 g, 1.9 mmol). The argon was evacuated and replaced by a balloon of H2. The reaction was stirred overnight and the catalyst removed by filtration. The solvent was evaporated under reduced pressure to give the desired aniline as a yellow solid (24 g, 98% yield).

Workup

  1. customThe argon was evacuated
  2. customthe catalyst removed by filtration
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-316b157488334204b684208ff160101c
Source dataset
uspto-grants-2009_10
Patent number
US07605175B2

Reaction notes

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