Water → 5-(Benzyloxy)-2-methoxyaniline

HRID 1707753Notes

Reaction equation

HRID 1707753 reaction equation
[Cl-].[NH4+].O.[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([N+:20]([O-])=O)[C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)C.[Zn]>[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[NH2:20])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 156769762-Nitro-4-phenylmethoxyanisole

Product 1

HCID 156769785-(Benzyloxy)-2-methoxyaniline

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

1.38 kg of zinc powder and 15 g of ammonium chloride in 3.25 litres of ethanol to which have been added 600 ml of water are heated to 80° C. 2.5 mole (648 g) of 3-benzyloxy-6-methoxynitrobenzene is added little by little. Stirring is continued for 15 minutes after the end of the addition. The zinc is removed by filtering the reaction medium hot. The product crystallizes from the filtrate by cooling. After centrifuging and then washing with petrol ether, the product is dried. It melts at 81° C.

Workup

  1. additionafter the end of the addition
  2. customThe zinc is removed
  3. filtrationby filtering the reaction medium hot
  4. customThe product crystallizes from the filtrate
  5. temperatureby cooling
  6. washwashing with petrol ether
  7. customthe product is dried

Sources & evidence

ORD record
ord-514b1587b89f4067abed8272e6917800
Source dataset
uspto-grants-1994_10
Patent number
US05354870

Reaction notes

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