Cyclohexene → 2-Amino-5-(dimethylamino)benzoic acid

HRID 1985676Notes

Reaction equation

HRID 1985676 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([N:13]([CH3:15])[CH3:14])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-])=O.C1CCCCC=1>C(O)C.[Pd]>[NH2:1][C:4]1[CH:12]=[CH:11][C:10]([N:13]([CH3:15])[CH3:14])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 127157935-(Dimethylamino)-2-nitrobenzoic acid

Product 1

HCID 127157942-Amino-5-(dimethylamino)benzoic acidYield 61.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The mixture of 2.1 g of 2-nitro-5-dimethylaminobenzoic acid, 7 mL of cyclohexene and 1.5 g of Pd/C (10%) is heated under reflux conditions in 60 mL of ethanol for 6 hours. The hot reaction mixture is filtered through celite filter. The filtrate is evaporated to obtain 1.1 g of the title compound. M.p.: 232° C.

Workup

  1. filtrationThe hot reaction mixture is filtered through celite filter
  2. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-470fc23f31cf4feab4f875cefc056b3e
Source dataset
uspto-grants-2009_06
Patent number
US07547696B2

Reaction notes

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