Benzyl Bromide → 4-Benzyloxy-2-nitroaniline

HRID 1757468Notes

Reaction equation

HRID 1757468 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(C(C)=O)C>[N+:1]([C:4]1[CH:10]=[C:9]([O:11][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 2614974-Benzyloxy-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

28.87 g (187.5 mM) of 2-nitro-4-hydroxyaniline in 600 ml of methyl ethyl ketone (MEK) are treated with 77.6 g of potassium carbonate and 22.3 ml (187.5 mM) of benzyl bromide. The reaction mixture is heated at reflux for3 h and is then evaporated to dryness. The evaporation residue is triturated in hexane, is filtered and dried under vacuum. There are thus isolated 40 g (88.9%) of the expected derivative, of melting point 106° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for3 h
  3. customis then evaporated to dryness
  4. customThe evaporation residue is triturated in hexane
  5. filtrationis filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-bdb4fd7dae9340d8b9add6230c52541b
Source dataset
uspto-grants-1995_08
Patent number
US05446059

Reaction notes

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