Acetic Acid → N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)benzene-1,2-diamine

HRID 240360Notes

Reaction equation

HRID 240360 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:20]=[CH:19][C:14]2[O:15][CH2:16][CH2:17][O:18][C:13]=2[CH:12]=1)([O-])=O.C(O)(=O)C.O>[Fe].C1(C)C=CC=CC=1>[O:15]1[CH2:16][CH2:17][O:18][C:13]2[CH:12]=[C:11]([NH:10][C:5]3[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:20]=[CH:19][C:14]1=2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 9185966N-(2-nitrophenyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-amine

Product 1

HCID 43148731N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)benzene-1,2-diamineYield 91.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 6.3 g (23 mmol) of N-(2-nitrophenyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-amine, 9.0 g (161 mmol) of iron powder, acetic acid (1 ml), water (35 ml) and toluene (70 ml) were heated to reflux for 8 hours. The reaction mixture was filtered aid to separate the waste. The organic layer of the filtrate was batched off, washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 5.1 g (yield: 91%) of N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)benzene-1,2-diamine) as a brown liquid.

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 8 hours
  3. filtrationThe reaction mixture was filtered aid
  4. customto separate the waste
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0388a403fe249a0ba76d66840988cb5
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Reaction notes

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