2-Methyl-2-(4-nitrophenyl)-1,3-dioxolane → 4-(2-Methyl-1,3-dioxolan-2-yl)aniline

HRID 450059Notes

Reaction equation

HRID 450059 reaction equation
[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1>C1C=CC=CC=1.O.[Fe]>[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[O:3][CH2:4][CH2:5][O:6]1

Participants

5

Reactant 1

HCID 6065982-Methyl-2-(4-nitrophenyl)-1,3-dioxolane

Product 1

HCID 110739824-(2-Methyl-1,3-dioxolan-2-yl)anilineYield 70%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 23925IronCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 2-methyl-2-(4-nitro-phenyl)-[1,3]dioxolane (100 mg, 0.48 mmol) in benzene (6 ml) was added iron powder (700 mg, 12.5 mmol) and 3 drops of water and then heated to reflux for 30 min. The reaction mixture was cooled, filtered and the filtrate was evaporated to give 4-(2-methyl-[1,3]-dioxolan-2-yl)-phenylamine (60 mg, 70%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 min
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-112b3f0fb0de402eb3f7e1fc270cb906
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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