HCID 59359507, compound → HCID 29066826, compound

HRID 383207Notes

Reaction equation

HRID 383207 reaction equation
[CH:1]([C:4]1[CH:19]=[CH:18][CH:17]=[CH:16][C:5]=1[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O)([CH3:3])[CH3:2].[H][H]>[Pd].C(O)C>[CH:1]([C:4]1[CH:19]=[CH:18][CH:17]=[CH:16][C:5]=1[NH:6][C:7]1[C:8]([NH2:13])=[CH:9][CH:10]=[CH:11][CH:12]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 59359507HCID 59359507, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 29066826HCID 29066826, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-isopropyl-N-(2-nitrophenyl)aniline (22.7 g, 89 mmol) and 10% palladium on carbon (0.6 g) were mixed with 150 mL of ethanol under nitrogen in a plastic coated hydrogenation vessel. The mixture was put on a par hydrogenator and reacted under 40 psi of hydrogen until there is no pressure drop. The catalyst was filtered off through a Celite bed. The solvent was evaporated. The product was used for the next step without further purification. 20 g of desired product was obtained.

Workup

  1. filtrationThe catalyst was filtered off through a Celite bed
  2. customThe solvent was evaporated
  3. customThe product was used for the next step without further purification

Sources & evidence

ORD record
ord-e116bc82bdf44bab808d9ad1e82688cb
Source dataset
uspto-grants-2013_02
Patent number
US08367223B2

Reaction notes

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