N-cyclopropyl-2-nitroaniline → N-cyclopropylbenzene-1,2-diamine

HRID 718086Notes

Reaction equation

HRID 718086 reaction equation
[CH:1]1([NH:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N+:11]([O-])=O)[CH2:3][CH2:2]1.[H][H]>[Pd].C(O)C>[CH:1]1([NH:4][C:5]2[C:6]([NH2:11])=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 10487549N-cyclopropyl-2-nitroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 10582926N-cyclopropylbenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Title compound 380 (3.1 g, 17.4 mmol) and palladium on charcoal 10% (0.3 g, 10% w/w) were mixed in ethanol (100 mL) and the reaction mixture was stirred under 45 PSI of hydrogen for 4 hours. The mixture was filtered to remove the catalyst and the filtrate was evaporated to afford title compound 381 as black oil that was used without further purification. MS (m/z): 148.9 (M+H).

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the catalyst
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-47a1a1ac3b564628b08ffcaf1f54bd8d
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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