Ammonia → 2-Amino-5-Nitrophenol

HRID 1533829Notes

Reaction equation

HRID 1533829 reaction equation
C1O[C:8]2[CH:7]=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=2[O:2]1.[NH3:13].COCCOCCOC>O>[NH2:13][C:8]1[CH:7]=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[OH:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8150DiglymeHCID 757981,3-Benzodioxole, 5-nitro-

Product 1

HCID 49847212-Amino-5-Nitrophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 0.18 mol (30 g) of 3,4-methylenedioxynitrobenzene in a mixture of 240 ml of 28% strength ammonia solution and 240 ml of diethylene glycol dimethyl ether is heated at 100° C. for 28 hours in an autoclave. After cooling, 480 ml of water are added. The unreacted initial product precipitates. It is recovered by filtration and the filtrate is then neutralised with hydrochloric acid. After filtration, the filtrate is extracted with ethyl acetate. The ethyl acetate is driven off in vacuo. The residue is treated with 25 ml of acetic anhydride and then kept in a boiling water-bath for 30 minutes. After cooling, the expected product is isolated in the form of the acetyl derivative. This acetyl derivative is hydrolysed with 45 ml of hydrochloric acid of density 1.17, at 90° C. for one hour. After dilution and neutralisation of the solution containing hydrochloric acid, 2-amino-5-nitrophenol is isolated by filtration.

Workup

  1. temperatureAfter cooling
  2. customThe unreacted initial product precipitates
  3. filtrationIt is recovered by filtration
  4. filtrationAfter filtration
  5. extractionthe filtrate is extracted with ethyl acetate
  6. additionThe residue is treated with 25 ml of acetic anhydride
  7. temperatureAfter cooling

Sources & evidence

ORD record
ord-3e416c1b50db468da95f530a44973f82
Source dataset
uspto-grants-1992_02
Patent number
US05085666

Reaction notes

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