Hydrochloric Acid → 4-(Benzyloxy)benzene-1,2-diamine

HRID 1064872Notes

Reaction equation

HRID 1064872 reaction equation
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([N+:16]([O-])=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)(=O)C.[Zn]>[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([NH2:16])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 2614974-Benzyloxy-2-nitroaniline

Product 1

HCID 131622394-(Benzyloxy)benzene-1,2-diamineYield 99.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-benzyloxy-2-nitroaniline (2.31 g, 9.46 mmol) in acetic acid (50 ml) was added conc. hydrochloric acid (1 ml), and gradually added zinc powder (2.16 g, 0.330 mmol) with ice-cooling and the mixture was stirred for 15 minutes, and further added gradually zinc powder (2.16 g, 0.33 mmol) and stirred for 20 minutes. The reaction solution was filtered with celite, and the filtrate was concentrated in vacuo. The resulting residue was dissolved in chloroform and neutralized with a saturated sodium bicarbonate solution. The organic layer was washed with water and a saturated sodium chloride solution successively, dried over anhydrous sodium sulfate and concentrated in vacuo to provide 2.01 g (yield 99%) of crude 4-benzyloxy-1,2-phenylenediamine.

Workup

  1. temperaturecooling
  2. stirringstirred for 20 minutes
  3. filtrationThe reaction solution was filtered with celite
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe resulting residue was dissolved in chloroform
  6. washThe organic layer was washed with water
  7. dry with materiala saturated sodium chloride solution successively, dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-80ad309f885941d2bb7c09cf08b18cf9
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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