HC Yellow no. 14 → 3-Amino4-(2-hydroxyethylamino)benzonitrile

HRID 412552Notes

Reaction equation

HRID 412552 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[N+:13]([O-])=O.O.O.[Sn](Cl)(Cl)(Cl)Cl>C(O)C>[NH2:13][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:5]=1[NH:4][CH2:3][CH2:2][OH:1])[C:9]#[N:10]

Participants

4

Reactant 2

HCID 15001944HC Yellow no. 14HCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 185364343-Amino4-(2-hydroxyethylamino)benzonitrileYield 78.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(2-hydroxyethylamino)-3-nitrobenzonitrile (3.11 g) and tin chloride dihydrate (16.94 g) in ethanol (50 ml) was stirred at 70° C. for 1 hour. After completion of the reaction, the solvent was evaporated and to the obtained residue were added tetrahydrofuran and 15% aqueous sodium hydroxide solution. The mixture was stirred and insoluble material and the aqueous layer were removed. The obtained organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated. The obtained solid was washed with chloroform, filtrated and dried under reduced pressure to give the title compound (2.08 g).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated and to the obtained residue
  3. additionwere added tetrahydrofuran and 15% aqueous sodium hydroxide solution
  4. custominsoluble material and the aqueous layer were removed
  5. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. washThe obtained solid was washed with chloroform
  8. filtrationfiltrated
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-7f4681a59657438b9c55441c2feb7f80
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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