Sodium Azide → 2-Nitro-4-chloro-5-allyloxyaniline

HRID 1957472Notes

Reaction equation

HRID 1957472 reaction equation
[CH2:1]([O:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([N+:12]([O-:14])=[O:13])=[C:7](Cl)[CH:6]=1)[CH:2]=[CH2:3].[N-:16]=[N+]=[N-].[Na+].[N-]=[N+]=[N-].[BH4-].[Na+]>CN(C=O)C>[N+:12]([C:8]1[CH:9]=[C:10]([Cl:11])[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[CH:6][C:7]=1[NH2:16])([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 4311764Sodium borohydride2×HCID 190676764-Allyloxy-2,5-dichloronitrobenzene

Product 1

HCID 190676752-Nitro-4-chloro-5-allyloxyanilineYield 82.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of step (b) (66.1 g, 267 mmol) was dissolved in 600 ml DMF at ambient temperature. Sodium azide (19.1 g, 267 mmol) was added and the mixture allowed to stir over a 4-day weekend, after which another 2 g (30.8 mmol) of the azide were added. Sodium borohydride (2.77 g, 73.5 mmol) was added in small portions while cooling in an ice bath. The mixture was stirred over night and then another 0.85 g (0.015 m) of sodium borohydride were added portionwise to the cold mixture. When the reaction appeared complete, the mixture was poured over ice water, the product filtered and dried to yield 50.5 g of 2-nitro-4-chloro-5-allyloxyaniline.

Workup

  1. temperaturewhile cooling in an ice bath
  2. stirringThe mixture was stirred over night
  3. filtrationthe product filtered
  4. customdried

Sources & evidence

ORD record
ord-c0d52dbb69c54927b95ecce7dcdd6b03
Source dataset
uspto-grants-1998_07
Patent number
US05786301

Reaction notes

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