Water → HCID 12445399, compound

HRID 240358

Reaction equation

HRID 240358 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:19]=[CH:18][C:14]2[O:15][CH2:16][O:17][C:13]=2[CH:12]=1)([O-])=O.C(OCC)(=O)C.O>[Fe].C(O)(=O)C>[O:15]1[C:14]2[CH:18]=[CH:19][C:11]([NH:10][C:5]3[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:12][C:13]=2[O:17][CH2:16]1

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 7922985N-(2-nitrophenyl)benzo[d][1,3]dioxol-5-ylamine

Product 1

HCID 12445399HCID 12445399, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

13.6 g (244 mmol) of iron powder and 10.5 g (40 mmol) of N-(2-nitrophenyl)benzo[d][1,3]dioxol-5-ylamine were added to a solvent mixture of ethyl acetate (130 ml), water (65 mL) and acetic acid (15 mL), and the mixture was stirred for 1 hour at 70° C. The reaction solution was cooled to room temperature, and the waste was separated by filtration using a filter aid. The organic layer of the filtrate was batched off, washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 9.2 g (yield: 99%) of N-(benzo[d][1,3]dioxol-5-yl)benzene-1,2-diamine as white crystals.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe waste was separated by filtration
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3dcdf96401424292ba6f3b0c12a2ef12
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Linked notes

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