Potassium Hydroxide → 3-(2-Amino-benzyl)thiophene

HRID 1076975Notes

Reaction equation

HRID 1076975 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)=O.[OH-].[K+].O.NN>C(O)COCCO>[NH2:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4][C:6]1[CH:10]=[CH:9][S:8][CH:7]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 127505413-(Amino-benzoyl)thiophene

Product 1

HCID 127505613-(2-Amino-benzyl)thiophene

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

14.8 g of 3-(amino-benzoyl)thiophene, 23.8 g of solid potassium hydroxide and 19.6 g of hydrazine hydrate are heated to the boil at reflux in 180 cc of diethylene glycol for 3 hours. After diluting the reaction mixture with ice water, extraction is effected with ether. The ether phase is washed thrice with water, is dried with sodium sulphate and concentrated. 3-(2-amino-benzyl)thiophene is obtained in the form of a light yellow oil having a B.P. of 121°-123° 10.05 mm Hg.

Workup

  1. additionAfter diluting the reaction mixture
  2. extractionwith ice water, extraction
  3. washThe ether phase is washed thrice with water
  4. dry with materialis dried with sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-65be94c783ec478c9d728355b674629b
Source dataset
uspto-grants-1976_05
Patent number
US03959282

Reaction notes

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